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

HRID 30601

Reaction equation

HRID 30601 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9250e28ef0964ab3b68b4b1dfcef66c5
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Linked notes

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