Water → 2,2-Difluoro-1-[4-(dimethylamino)phenyl]-2-phenylethanone

HRID 1463372

反応式

HRID 1463372 の反応式
Br[C:2]1[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[F:16][C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([F:21])[C:18]([O-])=[O:19].O>O1CCCC1.CCCCC>[F:16][C:17]([F:21])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:18]([C:2]1[CH:10]=[CH:9][C:5]([N:6]([CH3:8])[CH3:7])=[CH:4][CH:3]=1)=[O:19]

参加物

7

反応物 4

HCID 962WaterHCID 114654-bromo-N,N-dimethylanilineHCID 6928296alpha,alpha-DifluorophenylacetateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 157284592,2-Difluoro-1-[4-(dimethylamino)phenyl]-2-phenylethanone収率 31.8%

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

A solution of 4.0 g of 4-bromo-N,N-dimethylaniline in 50 ml of dry tetrahydrofuran at -78° C. was treated with 23.5 ml of 1.7M tert-butyllithium in pentane under nitrogen over 5 minutes with rapid stirring. After 0.5 hour, the slurry was warmed to -30° C. and added to a solution of 4.0 g of α,α-difluorophenylacetate in 50 ml of dry tetrahydrofuran at -78° C. After 1 hour at -78° C., the solution was allowed to warm to room temperature and stirred overnight. The solution was poured into water and extracted with ethyl acetate. Evaporation left a solid which was purified by flash chromatography (1:1 ethyl acetate-hexane) to give a powder. Recrystallization from ethyl acetate-hexane gave 1.75 g of 2,2-difluoro-1-[4-(dimethylamino)phenyl]-2-phenylethanone, m.p. 115°-116° C.

後処理

  1. waitAfter 1 hour at -78° C.
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. customEvaporation
  5. waitleft a solid which
  6. customwas purified by flash chromatography (1:1 ethyl acetate-hexane)
  7. customto give a powder
  8. customRecrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-71d03801ba0c44c28351c7f44d9df3e2
出典データセット
uspto-grants-1994_04
特許番号
US05300527

関連ノート

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