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

HRID 1824620ノート

反応式

HRID 1824620 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 110331771-Iodo-4(S-acetylthio)benzene収率 85.6%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒2 回HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e5a30f7de9654542bc19dbf13ecb0ce4
出典データセット
uspto-grants-2006_05
特許番号
US07042755B1

反応ノート

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