Phosphorus tribromide → 4-(Bromomethyl)-3-(trifluoromethyl)phenyl phenylmethyl ether

HRID 1946375ノート

反応式

HRID 1946375 の反応式
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:22].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:22])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 595479924-Benzyloxy-2-(trifluoromethyl)benzayl alcohol

生成物 1

HCID 667703034-(Bromomethyl)-3-(trifluoromethyl)phenyl phenylmethyl ether

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a solution of [4-[(phenylmethyl)oxy]-2-(trifluoromethyl)phenyl]methanol (for a preparation see Intermediate 18)(3.11 g, 11.02 mmol) in DCM (40 ml) under nitrogen in an ice-water bath was added a solution of phosphorus tribromide (1.09 ml, 11.6 mmol, Aldrich) in DCM (20 ml). The solution was allowed to warm to ambient temperature and stirred for 1.5 h. The reaction mixture was poured onto ice-water (150 ml) and saturated aqueous sodium hydrogen carbonate (75 ml). The mixture was diluted with dichloromethane (100 ml), and the phases separated. The aqueous extract was washed with dichloromethane (50 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give 4-(bromomethyl)-3-(trifluoromethyl)phenyl phenylmethyl ether as a white solid (2.96 g).

後処理

  1. customthe phases separated
  2. extractionThe aqueous extract
  3. washwas washed with dichloromethane (50 ml)
  4. washThe combined organic extracts were washed with water (50 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-b72b3cff62a14a51ab68b2b7d4460b63
出典データセット
uspto-grants-2013_03
特許番号
US08399436B2

反応ノート

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