Allyl Mercaptan → Methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate

HRID 1492389노트

반응식

HRID 1492389 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH2:14]([SH:17])[CH:15]=[CH2:16].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][S:17][CH2:14][CH:15]=[CH2:16])[CH:3]=1

참가 물질

6

반응물 4

HCID 13367Allyl MercaptanHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

생성물 1

HCID 18950273Methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate수율 10%

시약·촉매·용매 1

HCID 67553Tetrabutylammonium Iodide촉매

실험 절차

Methyl 4-bromo-2-bromomethylbenzoate (24.6 g) was added to a stirred mixture of allylmercaptan (70%, 9 g), sodium ethoxide (5.77 g) and tetrabutylammonium iodide (0.4 g) for 15 minutes. Cold sodium bicarbonate solution was added and the mixture extracted with ether. The extract was washed with brine, dried (magnesium sulphate) and evaporated to give methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate (2.41 g), NMR (CDCl3) 3.05 (d,2H), 3.9 (s,3H), 4.0 (s,2H), 5.1 (m,2H), 5.75 (m,1H), 7.4 (d,1H), 7.5 (s,1H), 7.75 (d,1H).

후처리

  1. extractionthe mixture extracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated

출처 및 근거

ORD 기록
ord-d7cd7ea48f184acea3b6cd632c82a8b2
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374606

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