Potassium Carbonate → 1-Bromo-4-(3-chloro-4-(trifluoromethyl)benzyloxy)-2,5-difluorobenzene

HRID 508428ノート

反応式

HRID 508428 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH2:5]Br.[Br:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([OH:22])=[C:17]([F:23])[CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:14][C:15]1[CH:16]=[C:17]([F:23])[C:18]([O:22][CH2:5][C:4]2[CH:7]=[CH:8][C:9]([C:10]([F:13])([F:12])[F:11])=[C:2]([Cl:1])[CH:3]=2)=[CH:19][C:20]=1[F:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 70180424-Bromo-2,5-difluorophenolHCID 235127654-(Bromomethyl)-2-chloro-1-(trifluoromethyl)benzene

生成物 1

HCID 866825541-Bromo-4-(3-chloro-4-(trifluoromethyl)benzyloxy)-2,5-difluorobenzene収率 99%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To solution of 3-chloro-4-(trifluoromethyl)benzyl bromide (300 mg, 1.097 mmol) in acetone (15 mL) was added 4-bromo-2,5-difluorophenol (1.097 mmol) followed by potassium carbonate (303 mg, 2.194 mmol). The reaction mixture was heated at reflux for 3.5 hours and then allowed to cool to room temperature. The solvent was removed under reduced pressure to yield a white solid, which was partitioned with water/EtOAc mixture (1:1, 50 mL). The organic layer was separated and the aqueous was extracted with EtOAc (3×30 mL). The combined organics were washed with brine (50 mL), dried over sodium sulphate, filtered and concentrated in vacuo to give the title compound as a white solid (434 mg, 99%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3.5 hours
  3. customThe solvent was removed under reduced pressure
  4. customto yield a white solid, which
  5. customwas partitioned with water/EtOAc mixture (1:1, 50 mL)
  6. customThe organic layer was separated
  7. extractionthe aqueous was extracted with EtOAc (3×30 mL)
  8. washThe combined organics were washed with brine (50 mL)
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e88892a6c818425ea4627e54c290cd81
出典データセット
uspto-grants-2015_08
特許番号
US09096500B2

反応ノート

読み込み中…