Methyl 3-chloro-2,4-dimethyl-6-(phenylsulfanyl)benzoate (5c): Starting with 4c (621 mg, 3.0 mmol), 3a (562 mg, 2.0 mmol), TiCl4 (0.32 mL, 3.0 mmol) and CH2Cl2 (11 mL), 5c was isolated as a highly viscous oil (350 mg, 57%). 1 H NMR (250 MHz, CDCl3): δ = 2.23 (s, 3 H, CH3), 2.28 (s, 3 H, CH3), 3.79 (s, 3 H, OCH3), 7.01 (s, 1 H, ArH), 7.16 (m, 2 H, ArH), 7.33 (m, 2 H, ArH). 13 S O OMe Me Cl Me C NMR (75 MHz, CDCl3): δ = 18.1, 20.8 (CH3), 52.3 (OCH3), 127.0 (ArCH), 129.1 (2C ArCH), 130.0 (C), 130.5 (2C ArCH), 133.0 (ArCH), 135.0 135.7, 135.8, 136.6, 138.4, 168.3 (C). IR (neat): ν̃ = 3382 (w), 2898 (s), 1722 (m), 1663 (s), 1534 (m), 1434 (m), 1321 (s), 1223 (s), 1123 (m), 1024 (m), 768 (w), 713 (m) cm −1 . GC-MS (EI, 70 eV): m/z (%): 308 (M + , 37 Cl, 37), 306 (M + , 35 Cl, 41), 267 (100), 105 (89), 77 (34). HRMS (EI): calcd for C15H17O2ClS [M + , 35 Cl]: 306.06127, found 306.06139. Methyl 2,4-dimethyl-3,6-bis(phenylsulfanyl)benzoate (5d): Starting with 4d (840 mg, 3.0 mmol), 3a (562 mg, 2.0 mmol), TiCl4 (0.32 mL, 3.0 mmol), and CH2Cl2 (11 mL), 5d was isolated as a highly viscous oil (485 mg, 63%). 1 S O OMe H NMR (250 Me SPh Me MHz, CDCl3): δ = 2.23 (s, 3 H, CH3), 2.35 (s, 3 H, CH3), 3.81 (s, 3 H, OCH3), 6.87 (s, 1 H, ArH), 7.03 (m, 3 H, ArH), 7.11 (m, 2 H, ArH), 7.23 (m, 3 H, ArH), 7.34 (m, 2 H, ArH). 13 C NMR (62 MHz, CDCl3): δ = 19.1, 22.1 (CH3), 52.1 (OCH3), 125.1 (ArCH), 125.9 (2C, ArCH), 127.7 (ArCH), 129.0 (2C, ArCH), 129.3 (2C, ArCH), 130.0 (C), 131.2 (ArCH), 132.0 (2C, ArCH), 134.5, 134.9, 135.1, 136.9, 141.1, 145.8, 168.8 (C). IR (neat): ν̃ = 3056 (w), 2938 (w), 1721 (s), 1685 (m), 1512 (m), 1423 (m), 1236 (s), 1149 (s), 1056 (s), 728 (s), 681 (s), 538 (m) cm −1 . GC-MS 44
(EI, 70 eV): m/z (%): 380 (100), 213 (26), 182 (25), 153 (16), 139 (20), 108 (8). HRMS (EI): calcd for C22H20O2S2 ( [M + ]: 380.06225, found 380.06228. Me S O nPr OMe Methyl 4-methyl-6-(phenylsulfanyl)-6-propylbenzoate (5e): Starting with 4e (600 mg, 3.0 mmol), 3a (562 g, 2.0 mmol), TiCl4 (0.32 mL, 3.0 mmol), and CH2Cl2 (11 mL), 5e was isolated as a highly viscous oil (255 mg, 42%). 1 H NMR (250 MHz, CDCl3): δ = 0.85 (t, 3 H, J = 7.1 Hz, CH3), 1.47 (m, 2 H, CH2), 2.11 (q, 2 H, J = 6.4 Hz, CH3), 2.24 (s, 3 H, CH3), 3.80 (s, 3 H, OCH3), 6.91 (s, 1 H, ArH), 7.16 (m, 2 H, ArH), 7.33 (m, 2 H, ArH). 13 C NMR (62 MHz, CDCl3): δ = 13.5, 19.7 (CH3), 24.3, 36.7 (CH2), 52.0 (OCH3), 126.8 (ArCH), 129.0 (2C ArCH), 129.5 (C), 130.0 (ArCH), 131.3 (2C ArCH), 135.5 (ArCH), 136.1 139.9, 144.8, 160.2, 165.8 (C). IR (neat): ν̃ = 3045 (w), 2978 (w), 1714 (s), 1675 (m), 1590 (s), 1460 (m), 1369 (s), 1269 (m), 1171 (m), 1024 (m), 751 (s) 690 (m) cm −1 . GC-MS (EI, 70 eV): m/z (%): 300 (40), 287 (46), 211 (23), 139 (23), 105 (23). HRMS (EI): calcd for C18H20O2S [M + ]: 300.03177, found 300.03156. 45
- Page 1 and 2: Synthesis of functionalized 2-(aryl
- Page 3 and 4: The ink of the scholar is more holy
- Page 5 and 6: Affectionately Dedicated to “All
- Page 7 and 8: Table of Contents 03 List of used a
- Page 9 and 10: RCM Ring Closing Metathesis TBAI Te
- Page 11 and 12: humans: 1) the thiomethyl of methio
- Page 13 and 14: Chart 3. Structure of sumatriptan S
- Page 15 and 16: disulfide (DADS) and diallyl sulfid
- Page 17 and 18: 1. Synthesis of functionalized 2-(a
- Page 19 and 20: 3-Arylthio-1-trimethylsilyloxy-1,3-
- Page 21 and 22: under kinetic reaction control, by
- Page 23 and 24: l a u 4-FC6H4 H Me H 40 m a v 4-FC6
- Page 25 and 26: Table 2. Synthesis of thioxanthones
- Page 27 and 28: 3a O OSiMe 3 O OMe + Me Me Cl 3TiO
- Page 29 and 30: Table 3. Synthesis of 8a-x 3 7 8 Ar
- Page 31 and 32: Cl + SPh OSiMe 3 3a 9 O OMe O O H i
- Page 33 and 34: solution. The use of an excess (1.5
- Page 35 and 36: Table 4. Synthesis of 12a-r 3 11 12
- Page 37 and 38: 2.3 Conclusion In conclusion, I hav
- Page 39 and 40: aromatization). An unseparable 1:2
- Page 41 and 42: Table 5. Synthesis of arenes 14a-l
- Page 43 and 44: 3.3 Conclusion In conclusion, I hav
- Page 45 and 46: Mass Spectroscopy: AMD MS40, AMD 40
- Page 47: 131.0 (ArCH), 132.7, 134.0, 135.9,
- Page 51 and 52: (m), 1490 (m), 1434 (m), 1383 (w),
- Page 53 and 54: 15.4, 16.9, 18.9 (CH3), 28.3 (CH2),
- Page 55 and 56: (C). IR (neat): ν̃ = 2945 (w), 29
- Page 57 and 58: 948 (w) 853 (m), 803 (m), 751 (m),
- Page 59 and 60: 135.4, 139.2, 143.8, 146.5, 182.2 (
- Page 61 and 62: Me S O Me Ph Br Methyl 4-methyl-5-(
- Page 63 and 64: 35 Cl, 37 Cl, 61), 430 (M + , 35 Cl
- Page 65 and 66: ArH). 13 C NMR (62 MHz, CDCl3): δ
- Page 67 and 68: Me S O Me Me Methyl 4,6-dimethyl-5-
- Page 69 and 70: S Methyl 4-methyl-5-(2-bromoethyl)-
- Page 71 and 72: (CH2CH3), 33.3 (CH2), 40.1 (CH2), 5
- Page 73 and 74: Me 3,4-Dimethyl-2-phenylsulfanyl-be
- Page 75 and 76: Me 3,4-Dimethyl-2-(p-tolylsulfanyl)
- Page 77 and 78: OCH3), 7.08-7.17 (m, 7H, Ar); 13 C
- Page 79 and 80: (w), 750 (s), 732 (s), 688 (s), 650
- Page 81 and 82: 35 Cl 35 Cl, 100), 359 (26), 357 (3
- Page 83 and 84: 2924 (w), 2853 (w), 1728 (s), 1712
- Page 85 and 86: Me 3-Hydroxy-5-(4-methylphenylsulfa
- Page 87 and 88: Et 3-Hydroxy-5-(4-ethylphenylsulfan
- Page 89 and 90: (13), 264 (13), 262 (36) ,260 (12),
- Page 91 and 92: MS (EI, 70 eV): m/z (%) = 337 (16),
- Page 93 and 94: OH O 5'-Hydroxy-[1,1';3',1'']terphe
- Page 95 and 96: Refrences 1. Handbook of Chemistry
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Nationality Pakistan Place of Birth
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Publications 1. Inam Iqbal, Muhamma
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Tetrahedron 2007, 63, 12562-12575.