3-Chloro-2-methylthiophenol synthesis

Yield:-

Reaction Conditions:

with triphenylphosphine in 1,4-dioxane;water at 100; for 2 h;

Steps:

16.A
Example 16; Part A; A reaction mixture of 3-chloro-2-methylbenzene-1-sulfonyl chloride (0.9 g, 4 mmol) and triphenylphosphine (4.19 g, 16 mmol) in dioxane/water (4:1 , 20 mL) was stirred at 100 ⁰C for 2 hours. The mixture was diluted with water. The organic components were extracted with EtOAc twice. The combined EtOAc layers were concentrated. The residue was purified using chromatography. Compound 16-1 was eluted with 10% DCM in Hexane. Solvent evaporation afforded compound 16-1 as clear oil. ¹H NMR (400 MHz, CD₃OD) δ 7.17 (d, J = 8.4 Hz, 2H), 6.97 (t, J = 8.4 Hz, 1H), 3.43 (s, 1H), 2.40 (s, 3H).

References:

SCHERING CORPORATION;SHIPPS, JR., Gerald, W.;CHENG, Cliff, C.;HUANG, Xiaohua;ACHAB, Abdelghani, Abe;ORTH, Peter;VOIGT, Johannes, H.;SOUCY, Kyle, Ann WO2010/56631, 2010, A1 Location in patent:Page/Page column 116-117