Water → 2-Methyl-3-(methylthio)-4-(trifluoromethyl)benzoic acid

HRID 2079562ノート

反応式

HRID 2079562 の反応式
F[C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[H-].[Na+].[CH3:18][S-:19].[Na+].O>CN(C)C=O>[CH3:15][C:3]1[C:2]([S:19][CH3:18])=[C:10]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 4378561Sodium methanethiolateHCID 574577653-Fluoro-2-methyl-4-(trifluoromethyl)benzoic acid

生成物 1

HCID 574577672-Methyl-3-(methylthio)-4-(trifluoromethyl)benzoic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

300 mg (1.35 mmol) of 3-fluoro-2-methyl-4-trifluoromethylbenzoic acid were initially charged in 5 ml of N,N-dimethylformamide, and 59 mg (purity 60% by weight, 1.49 mmol) of NaH were added. The mixture was stirred for 10 min, and 199 mg (purity 95% by weight, 2.70 mmol) of sodium thiomethoxide were then added. The mixture was stirred at RT for 1.5 h and then heated at 80° C. for 16 h. The reaction mixture was cooled and, for workup, poured into water and extracted with ethyl acetate, and the aqueous phase was then acidified with concentrated HCl. The mixture was extracted twice with t-butyl methyl ether, dried and concentrated. This gave 310 mg of the product.

後処理

  1. stirringThe mixture was stirred at RT for 1.5 h
  2. temperatureThe reaction mixture was cooled and, for workup
  3. extractionextracted with ethyl acetate
  4. extractionThe mixture was extracted twice with t-butyl methyl ether
  5. customdried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-98ff123f92e342abb245b72f666a5357
出典データセット
uspto-grants-2011_04
特許番号
US07932211B2

反応ノート

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