Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
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1 Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br) Sridhar Madabhushi,* a Raveendra Jillella, a Vinodkumar Sriramoju a and Rajpal Singh b a Fluoroorganics Division, CSIR- Indian Institute of Chemical Technology, Hyderabad , India Tel.:( +91) ; fax: (+91) ; E- mail: smiict@gmail.com. b Centre for Fire Explosives and Environmental Safety, DRDO, Timarpur, New Delhi , India. Table of contents: 1. Procedure for preparation of sulfonyl halides 2a, 3a.S3 2. Characterization data for compounds 2a-n and 3a-f,... S 3 -S References for solid compounds, 2b, 2d, 2e, 2i, 3b, 3d, 3e.S H and 13 C NMR Spectra for compounds 2a-nand 3a-f S 11 -S 29 General Information: Oxone (2KHSO 5 KHSO 4 K 2 SO 4 ), N-chlorosuccinimide, KBr, were purchased from Sigma-Aldrich India Ltd.,. aq. HCl, aq. HBr, NaCl, KCl, KI and other solvents used in this study were procured from SD Fine Chem. Ltd., India. Melting points of the compounds were recorded on Veego programmable melting point apparatus in open capillaries and are uncorrected. IR spectra were recorded on a PerkinElmer FT-IR 240-C spectrophotometer using KBr & neat optics. 1 H NMR spectra were recorded on Bruker AV 300 MHz in CDCl 3 using TMS as the internal standard. All the reactions were monitored by thin layer chromatography (TLC) on precoated silica gel 60 F254 (mesh); spots were visualized S 1
2 with UV light or by charring with anisaldehyde solution. Merck silica gel ( mesh) was used for column chromatography. General procedure for the preparation of sulfonyl chlorides with oxone-kx: A mixture of thiol (3.4 mmol), oxone (8.6 mmol) and KCl (3.4 mmol), water (10 ml) was taken into a round bottomed flask and stirred at room temperatur. This reaction is slightly exothermic and temperature of the mixture rose to 45 o C. After completion of the reaction (TLC), the reaction mixture was extracted with ethyl acetate (4x5 ml). The combined organic layers was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product obtained was purified by normal column chromatography (silica gel mesh, n-hexane) to obtain corresponding sulfonyl chloride. A similar procedure was used for preparation of sulfonyl bromides with oxone-kbr. General procedure for the preparation of sulfonyl chlorides from disulfides: A mixture of disulfide (1.7 mmol), oxone (3.5 mmol) and KCl (3.5 mmol), water (10 ml) was taken into a round bottomed flask and stirred at room temperature. After completion of the reaction (TLC), the reaction mixture was extracted with ethyl acetate (4x5 ml) and the combined organic layer was dried over anhydrous Na 2 SO 4 and concentrated under reduced pressure. The crude product obtained was purified by normal column chromatography (silica gel mesh, n-hexane) to obtain corresponding sulfonyl chloride. Characterization data: SO 2 Cl 2a Benzenesulfonyl chloride (2a). Colorless oil, (0.31 g, 98%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), 7.76 (t, J = 7.3 Hz, 1H), 7.62 (t, J = 7.7 Hz, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ =136.4, 133.6, 131.3, 129.3, 128.7, 127.4; IR (neat): υ 3065, S 2
3 2926, 2855, 1444, 1326, 1144, 1077, 750, 593 cm -1. EI-MS 176, 159, 112, 95, 75, 57; EI- HRMS: Exact mass observed for C 6 H 5 ClO 2 S: (calculated: ). SO 2 Cl Cl 2b 4-chlorobenzene-1-sulfonyl chloride (2b). White solid, m.p o C (lit ) (0.28 g, 97%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.98 (d, J = 8.6 Hz, 2H) 7.60 (d, J = 8.6 Hz, 2H), 13 C NMR (75 MHz, CDCl 3 ): δ = 142.4, 140.4, 137.6; IR (neat): υ 3109, 3052, 1573, 1474, 1184, 1088, 825, 755, 559 cm -1. EI-MS 212, 201, 177, 175, 111, 75, 69; EI- HRMS: Exact mass observed for C 6 H 4 Cl 2 O 2 S: (calculated: ). F SO 2 Cl 2c 3-Fluorobenzene-1-sulfonyl chloride (2c). Pale yellow solid m.p o C, (0.28 g, 95%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.98 (d, J = 8.1 Hz, 2H), 7.30 (d, J = 8.1 Hz, 2H), 6.69 (s, 1H), 2.44 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ = 185.5, 145.6, 129.7, 129.5, 128.0, 39.9, 21.7; IR (neat): υ 3108, 3056, 2927, 2757, 1593, 1474, 1368, 1228, 1163, 884, 595 cm -1. EI-HRMS: Exact mass observed for C 6 H 4 ClFO 2 S: (calculated: ). SO 2 Cl 2d 4-Methylbenzene-1-sulfonyl chloride (2d): White solid m.p o C (lit ) (0.29 g, 96%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.89 (d, J = 8.4 Hz, 2H), 7.43 (d, J = 8.4 Hz, 2H), 2.59 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ =146.8, 130.2, 126.9, 21.7; IR (KBr): S 3
4 υ 3009, 1690, 1598, 1481, 1231, 993, 796, cm -1. EI-MS 191, 175, 128, 111, 75, 55; EI-HRMS: Exact mass observed for C 7 H 7 ClO 2 S: (calculated: ). SO 2 Cl 2e Naphthalene-1-sulfonyl chloride (2e). White solid, m.p o C (lit ); (0.25 g, 92%). 1 H NMR (300 MHz, CDCl 3 ): δ = 8.61 (s, 1H), (m, 4H), (m, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ= 130.3, 130.2, 129.8, 128.9, 128.3, 128.1, 121.2; IR (neat): υ 3108, 3073, 2928, 1589, 1492, 1380, 1182, 1081, 840 cm -1. EI-MS: 226, 210, 208, 146, 127, 115, 77, 57; EI-HRMS: Exact mass observed for C 10 H 7 ClO 2 S: (calculated: ). SO 2 Cl 2f Cyclohexanesulfonyl chloride (2f). Colorless oil (0.27 g, 89%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ = 74.7, 27.0, 24.8, 24.5; IR (neat): υ 2938, 2859, 1451, 1369, 1219, 1160, 751, 589 cm -1 ; EI-MS: m/z. 182, 118, 99, 83, 67, 55; EI- HRMS: Exact mass observed for C 6 H 11 ClO 2 S : (caluculated: ). SO 2 Cl F 2g 44-Fluorobenzene-1-sulfonyl chloride (2g). Colorless oil (0.28 g, 95). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ = 168.1, 130.1, 130.0, 117.2, 116.9; IR (neat): υ 3108, 3073, 2928, 1589, 1492, S 4
5 1380, 1182, 840, 569 cm -1. EI-HRMS: Exact mass observed for C 6 H 4 ClFO 2 S: (calculated: ). Cl SO 2 Cl F 2h 3-Chloro-4-fluorobenzene-1-sulfonyl chloride (2h).Colorless oil (0.25 g, 92). 1 H NMR (300 MHz, CDCl 3 ): δ = 8.14 (dd, J = 2.4 Hz, 1H), (m, 1H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ =163.7, 130.1, 127.8, 127.6, 118.2, 117.8; IR (neat): υ 2927, 2757, 1593, 1474, 1228, 1163, 1101, 884 cm -1. EI-MS: 227, 224, 195, 193, , 109, 94, 79; EI-HRMS: Exact mass observed for C 6 H 3 Cl 2 FO 2 S: (calculated: ). MeO SO 2 Cl MeO 2i 3,4-Dimethoxybenzene-1-sulfonyl chloride (2i). White solid, 63-65, (lit ), (0.24 g, 90%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.68 (dd, J = 2.2 Hz, 1H), 7.44 (d, J = 2.2 Hz, 1H), 7.68 (d, J = 8.5 Hz, 1H), 3.99 (s, 3H), 3.97 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ =154.6, 149.2, 135.8, , , 56.3; IR (neat): υ 2929, 2862, 1461, 1406, 1229, 1183, 1119, 1034, 819 cm -1. EI-MS: 236, 201, 153, 137, 94, 79; EI-HRMS: Exact mass observed for C 8 H 10 ClO 4 S: (calculated: ). S 5
6 N 2j SO 2 Cl Pyridine-2-sulfonyl chloride (2j). Colorless oil (0.28 g, 88%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 1H), (m, 3H); 13 C NMR (75 MHz, CDCl 3 +DMSO-D 6 ): δ = 155.2, 146.0, 140, 126.1, 123.3; IR (neat): υ 3029, 1453, 1028, 638 cm -1.EI-MS 177, 175, 159, 111, 69, 57; EI-HRMS: Exact mass observed for C 5 H 4 ClO 2 S: (calculated: ). SO 2 Cl F 3 C 2k 4-(Trifluoromethyl)benzene-1-sulfonyl chloride (2k): Colourless oil (024 g, 90%). 1 H NMR (300 MHz, CDCl 3 ): δ = 8.20 (d, J = 8.3 Hz, 2H), 7.92 (d, J = 8.3 Hz, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ = 147.0, , 136.1, 127.6, 127.0, 126.9; IR (neat): υ 3026, 1454, 1242, 1145, 1014, 940, 780 cm -1 ; EI-HRMS: Exact mass observed for C 7 H 4 ClF 3 O 2 S: (calculated: ). SO 2 Cl MeO 2l 4-Methoxybenzene-1-sulfonyl chloride (2l). Colorless oil (0.27 g, 93%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.97 (d, J = 9.0 Hz, 2H), 7.04 (d, J = 9.0 Hz, 2H), 3.92 (s, 3H) 13 C NMR (75 MHz, CDCl 3 ): δ = 159.8, 132.6, 128.3, 114.5, 55.3; IR (neat): υ 3052, 3007, 2926, 2854, 1574, 1463, 1367, 1281, 1171, 1088, 944 cm -1. EI-MS 206, 190, 175, 142, 75, 55; EI-HRMS: Exact mass observed for C 7 H 7 ClO 3 S: (calculated: ). S 6
7 CH 3 N N N SO 2 Cl N 2m 1-Methyl-1H-tetrazole-5-sulfonyl chloride (2m). Colorless oil (0.27 g, 88%). 1 H NMR (300 MHz, CDCl 3 ): δ = (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ = ; IR (neat): υ 2928, 2858, 1633, 1343, 1056, 771cm -1. Mass: ESI-MS:181(M+H), 203 (M+Na). 2n SO 2 Cl Hexane-1-sulfonyl chloride (2n). Colorless oil (0.21 g, 68). 1 H NMR (300 MHz, CDCl 3 ): δ = 3.38 (t, J = 7.3, 7.4 Hz, 2H), (m, 2H), (m, 6H), 0.89 (t, J = 6.6, 6.7 Hz, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ = 62.5, 36.1, 31.0, 23.3, 22.3, 13.8; IR (neat): υ 2929, 2857, 1463, 1378, 1256, 988, 725 cm -1. EI-MS 184, 141, 125, 109, 77, 69, 57; EI-HRMS: Exact mass observed for C 6 H 13 ClO 2 S: (calculated: ). SO 2 Br 3a Benzenesulfonyl bromide (3a). Colorless oil (0.38 g, 96%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), 7.76 (t, J = 7.3 Hz, 1H), 7.63 (t, J = 7.7 Hz, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ =136.4, 133.6, 131.3, 129.3, 128.7, 127.4; IR (neat): υ 3022, 2919, 1489, 1329, 1143, 806, 653 cm -1. EI-MS 220, 171, 158, 137, 97, 69; EI-HRMS: Exact mass observed for C 6 H 5 ClO 2 S: (calculated: ). SO 2 Br Cl 3b 4-Chlorobenzene-1-sulfonyl bromide (3b). White solid, m.p o C (lit ); (0.35 g, 95%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.98 (d, J = 8.6 Hz, 2H) 7.60 S 7
8 (d, J = 8.6 Hz, 2H), 13 C NMR (75 MHz, CDCl 3 ): δ = 142.4, 140.4, 130.0; IR (neat): υ 3109, 3052, 1573, 1474, 1184, 1088, 825, 755, 559 cm -1. EI-MS 256, 254, 177, 175, 113, 111, 75, 76; EI-HRMS: Exact mass observed for C 6 H 4 Cl 2 O 2 S: (calculated: ). F SO 2 Br 3c 3-Fluorobenzene-1-sulfonyl bromide (3c). Colorless oil (0.34 g, 92%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 2H), (m, 2H), (m, 1H); 13 C NMR (75 MHz, CDCl 3 ): δ = 163.5, 131.4, 122.7, 122.4, 114.1, 113.7; IR (neat): υ 3073, 2938, 1564, 1485, 1378, 1192, 846 cm -1. EI-HRMS: Exact mass observed for C 6 H 4 BrFO 2 S: (calculated: ). SO 2 Br 3d 4-Methylbenzene-1-sulfonyl chloride (3d). White solid m.p o C (lit ); (0.33 g, 89%). 1 H NMR (300 MHz, CDCl 3 ): δ = 7.87 (d, J = 8.0 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 2.46 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ =142.20, , , , 21.80; IR (KBr): υ 3010, 2923, 1584, 1457, 1027, 696 cm -1.EI-MS 234, 202, 186, 171, 139, 123, 107, 92, 77; EI-HRMS: Exact mass observed for C 7 H 7 BrO 2 S: (calculated: ). SO 2 Br 3e Naphthalene-2-sulfonyl bromide (3e). pale yellow solid m.p o C (lit ); (0.30 g, 90%). 1 H NMR (300 MHz, CDCl 3 ): δ = 8.62 (s, 1H), (m, 4H), S 8
9 (m, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ= 135.6, 132.1, 130.3, 130.1, 129.9, 128.3, 128.1, 121.0; IR (neat): υ 3063, 2946, 1589, 1455, 1237, 1025, 840 cm -1. EI-MS: 270, 185, 149, 139, 123, 69, 57; EI-HRMS: Exact mass observed for C 10 H 7 ClO 2 S: (calculated: ). SO 2 Br 3f Cyclohexanesulfonyl bromide (3f). Colorless oil (0.37 g, 95%). 1 H NMR (300 MHz, CDCl 3 ): δ = (m, 1H), (m, 2H), (m, 2H), (m, 3H), (m, 3H); 13 C NMR (75 MHz, CDCl 3 ): δ = 74.7, 27.0, 24.8, 24.5; IR (neat): υ 2938, 2859, 1451, 1369, 1219, 1160, 751, 589 cm -1 ; EI-MS: m/z. 227, 225, 191, 163, 148, 111, 97, 83, 69, 55; EI-HRMS: Exact mass observed for C 6 H 11 BrO 2 S: (caluculated: ). References: 1. K. Bahrami, M. M. Khodaei, M. Soheilizad, K. Donya, Tetrahedron Lett., 2012, 53, K. Bahrami, Synlett, 2011, 18, Anderson III, Jacob III, M. Castagnoli Jr, Shulgin, J, Medicinal, chem., 1977, 20, C. Stephen, D. Hamza, S. N. Wadman, Tetrahedron lett., 1999, 40, L. M. Litvinenko, V. A. Savelova, T. I. Krichevtsova, Zhurnal Obshchei Khimii., 1964, 34, S 9
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