4-Methyl-3-(trifluoromethyl)benzoic acid → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

HRID 1184845

反応式

HRID 1184845 の反応式
[Br:1]([O-])(=O)=O.[Na+].[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:19])([F:18])[F:17].S(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CCOCC>[Br:1][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([F:17])([F:18])[F:19]

参加物

7

反応物 3

HCID 27755924-Methyl-3-(trifluoromethyl)benzoic acidHCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

生成物 1

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acid収率 81.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of sodium bromate (1109 mg, 7.35 mmol) in H2O (3.3 mL) was added 4-methyl-3-trifluoromethyl-benzoic acid (500 mg, 2.449 mmol) in ethyl acetate (5 mL), followed by a solution of sodium bisulfite (765 mg, 7.35 mmol) in H2O (9 mL) over a period of about 15 min. The mixture was stirred overnight at room temperature and overnight at 50° C. The mixture was poured in ether (50 mL). The aqueous layer was extracted twice with ether and the combined organic layer was washed with anhydrous Na2S2O3 solution, dried, filtered and concentrated in vacuo to give the crude 4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 35 (563 mg, 81%) which was used without further purification. (m/z)=282 and 284 (M+H)+.

後処理

  1. extractionThe aqueous layer was extracted twice with ether
  2. washthe combined organic layer was washed with anhydrous Na2S2O3 solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-17e57dc3f99f4701b61acd8c4b8203f1
出典データセット
uspto-grants-2014_03
特許番号
US08669256B2

関連ノート

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