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

HRID 2111451노트

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HRID 2111451 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 23994Zinc촉매2회HCID 111,2-Dichloroethane용매HCID 962Water용매HCID 63651,1-Dichloroethane용매

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온도
50 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-69280f1049c74bf891f6707265cd1855
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07518905B2

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