Water → 1-(Benzyloxy)-3-bromo-2-fluorobenzene

HRID 2358126ノート

反応式

HRID 2358126 の反応式
[Br:1][C:2]1[C:3]([F:9])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CC(C)=O.C(OCC)(=O)C>[CH2:16]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 184012573-Bromo-2-fluorophenol

生成物 1

HCID 574388031-(Benzyloxy)-3-bromo-2-fluorobenzene収率 105.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3-bromo-2-fluorophenol (1.8 g, 9.42 mmol) in acetone (25 ml) was added sodium carbonate (2.55 g, 20 mmol) and the mixture was stirred for 5 min. Benzylbromide (1.2 ml, 10.3 mmol) was added and the reaction mixture was heated at reflux for 20 h. Water (50 ml) and ethyl acetate (50 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated under reduced pressure to give an oil. The residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1) to give the title compound (2.8 g). MS m/z (rel. intensity, 70 eV) 282 (M+, 2), 280 (M+, 2), 163 (2), 161 (2), 91 (bp).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 20 h
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic phases was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give an oil
  8. customThe residue was purified by flash column chromatography (isooctane/ethyl acetate, 5:1)

出典と根拠

ORDレコード
ord-6cf1694d88be4278911b3d2d249eaf8c
出典データセット
uspto-grants-2010_07
特許番号
US07763639B2

反応ノート

読み込み中…