Ammonium Chloride → (R)-2-fluoro-2-(3-bromophenyl)-1-ethanol

HRID 30601

反応式

HRID 30601 の反応式
[F:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[CH:3]=[O:4].[BH4-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.C(O)C>[F:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[CH2:3][OH:4]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86611665(R)-2-fluoro-2-(3-bromophenyl)acetaldehyde

生成物 1

HCID 68649207(R)-2-fluoro-2-(3-bromophenyl)-1-ethanol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of (R)-2-fluoro-2-(3-bromophenyl)acetaldehyde in CH2Cl2 and ethanol is treated with NaBH4 (189 mg, 5 mmol), stirred for 30 min, cooled to 0° C., treated with saturated NH4Cl, warmed to room temperature, stirred vigorously for 1 h at room temperature and diluted with CH2Cl2. The phases are separated. The aqueous phase is extracted with CH2Cl2. The organic phase and the extracts are combined, washed with NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by column chromatography (5% EtOAc and hexane as eluant)to give (R)-2-fluro-2-(3-bromophenyl)-1-ethanol.

後処理

  1. temperaturewarmed to room temperature
  2. stirringstirred vigorously for 1 h at room temperature
  3. customThe phases are separated
  4. extractionThe aqueous phase is extracted with CH2Cl2
  5. washwashed with NaHCO3 and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is purified by column chromatography (5% EtOAc and hexane

出典と根拠

ORDレコード
ord-9250e28ef0964ab3b68b4b1dfcef66c5
出典データセット
uspto-grants-2008_09
特許番号
US07423158B2

関連ノート

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