Acetyl chloride → 1-Iodo-4(S-acetylthio)benzene

Participants

Reaction Conditions

Reaction Steps

Following a general procedure (Uchiro and Kobayashi (1999) Tetrahedron Lett., 40: 3179–3182), to a stirred suspension of zinc powder (3.80 g, 58.0 mmol) and dichlorodimethylsilane (7.00 mL, 58.0 mmol) in 1,2-dichloroethane (126 mL) was added a solution of 4-iodobenzenesulfonyl chloride (5.00 g, 16.5 mmol) and N,N-dimethylacetamide (4.60 mL, 50.0 mmol) in dichloroethane (126 mL). The mixture was stirred at 75° C. for 2 h until the zinc powder was no longer visible. The reaction mixture was cooled to 50° C. and acetyl chloride (1.53 mL, 21.5 mmol) was added. After 15 min the mixture was poured into water. The water layer was extracted with CH2Cl2 and the combined organic layers were dried (Na2SO4), filtered and evaporated. The colorless oil thus obtained was chromatographed (silica, CH2Cl2/hexanes, 1:4) affording a colorless oil (3.93 g, 85.0%) which solidified at −20° C. mp 56–57° C. (lit. 54–55° C.)43; 1H NMR δ 2.42 (s, 3H), 7.12, 7.73 (AA′BB′, 2×2H); 13C NMR δ 31.0, 96.7, 128.4, 136.7, 139.0, 193.9; Anal. Calcd. for C8H7IOS: C, 34.55; H, 2.54; I, 45.63; S, 11.53; Found: C, 34.69; H, 2.59; I, 45.52; S, 11.59.

Provenance & Evidence