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

HRID 30601

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HRID 30601 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9250e28ef0964ab3b68b4b1dfcef66c5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

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