1-Chloro-1-(4-methoxyphenyl)-1-trifluoromethylethane → 1-Methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene

HRID 473360ノート

反応式

HRID 473360 の反応式
Cl[C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[C:3]([F:6])([F:5])[F:4].[CH3:16][Al](C)C>Cl>[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:2]([CH3:16])([CH3:7])[C:3]([F:6])([F:5])[F:4])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 138856001-Chloro-1-(4-methoxyphenyl)-1-trifluoromethylethaneHCID 16682925Trimethylaluminum

生成物 1

HCID 183336241-Methoxy-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒2 回

反応条件

温度
95 °C

実験手順

A solution of 1-(2-chloro-1,1,1-trifluoropropan-2-yl)-4-methoxybenzene (18.0 g, 75 mmol) in 400 ml of hexanes was treated with trimethylaluminum (151 ml, 302 mmol) (2.0 M in heptane) at rt and the resulting mixture was heated at 95° C. overnight. The reaction mixture was cooled in an ice-water bath, conc. HCl was added to the reaction mixture dropwise. Fumes were generated. After about 10 ml of conc. HCl was added, more rapid addition of acid was possible due to the near complete quenching of the unreacted AlMe3. After addition of 100 ml of conc. HCl, 250 ml of H2O was added and the mixture was stirred vigorously for 1 h. The layers were separated. The org layer was dried (Na2SO4) and concentrated to give the title compound as an oil, which solidified upon drying on the vac line.

後処理

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. additionmore rapid addition of acid
  3. customcomplete quenching of the unreacted AlMe3
  4. additionAfter addition of 100 ml of conc. HCl, 250 ml of H2O
  5. additionwas added
  6. customThe layers were separated
  7. dry with materialThe org layer was dried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-b3bf30cb2a3a4f228191372036b0d875
出典データセット
uspto-grants-2014_01
特許番号
US08633315B2

反応ノート

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