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

HRID 1492389ノート

反応式

HRID 1492389 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 67553Tetrabutylammonium Iodide触媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-d7cd7ea48f184acea3b6cd632c82a8b2
出典データセット
uspto-grants-1994_12
特許番号
US05374606

反応ノート

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