N-bromobutanimide → Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate

HRID 2121178ノート

反応式

HRID 2121178 の反応式
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][Br:20])=[CH:6][C:5]=1[O:11][S:12]([C:15]([F:17])([F:16])[F:18])(=[O:14])=[O:13]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

生成物 1

HCID 18474595Methyl 4-bromomethyl-2-trifluoromethylsulfonyloxybenzoate収率 80.2%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a stirred solution of 2-(trifluoromethanesulfonyloxy)-4-methylbenzoic acid methyl ester (19.6 g, 65.8 mmol), prepared as in Example 204A, in 250 mL CCl4 was added N-bromosuccinimide (12.29 g, 69.1 mmol) followed by 2,2′-azobisisobutyronitrile (108 mg, 0.658 mmol) and the reaction was heated to reflux. After 16 hours, the reaction was evaporated and the residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes) to give 19.9 g (80%) of 2-(trifluoromethanesulfonyloxy)-4-bromomethylbenzoic acid methyl ester as a yellow oil.

後処理

  1. temperaturethe reaction was heated to reflux
  2. customthe reaction was evaporated
  3. customthe residue was purified by flash chromatography over silica gel (10% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-021253110724429d8d88c46e39a6e0e1
出典データセット
uspto-grants-2004_02
特許番号
US06693123B2

反応ノート

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