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

HRID 1824620Notes

Reaction equation

HRID 1824620 reaction equation
Cl[Si](Cl)(C)C.[I:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=O)=O)=[CH:9][CH:8]=1.CN(C)[C:19](=[O:21])[CH3:20].C(Cl)(=O)C>ClCCCl.ClC(Cl)C.[Zn].O>[I:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:19](=[O:21])[CH3:20])=[CH:9][CH:8]=1

Participants

9

Reactant 4

HCID 6367Acetyl chlorideHCID 6398DichlorodimethylsilaneHCID 73994-Iodobenzenesulfonyl chlorideHCID 31374Dimethylacetamide

Product 1

HCID 110331771-Iodo-4(S-acetylthio)benzeneYield 85.6%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalyst2×HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  1. extractionThe water layer was extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe colorless oil thus obtained
  6. customwas chromatographed (silica, CH2Cl2/hexanes, 1:4)

Sources & evidence

ORD record
ord-e5a30f7de9654542bc19dbf13ecb0ce4
Source dataset
uspto-grants-2006_05
Patent number
US07042755B1

Reaction notes

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