Methanol → 1-(4-Bromo-2-chlorophenyl)ethanol

HRID 40277Notes

Reaction equation

HRID 40277 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([Cl:11])[CH:3]=1.[BH4-].[Na+].CO.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[C:4]([Cl:11])[CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-one

Product 1

HCID 202581281-(4-Bromo-2-chlorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

To a stirring solution of 1-(4-bromo-2-chlorophenyl)ethanone (700 mg, 2998 μmol) in THF (20 mL) was added sodium borohydride (340 mg, 8994 μmol) and methanol (5 mL). Reaction suspension stirred overnight at 30° C. Reaction then partioned between EtOAc (50 mL) and sat NH4Cl (25 mL). Aqueous further extracted with EtOAc (2×25 mL). Combined organics dried over MgSO4, concentrated, then purified on silica (40 g) eluting with 10>40% EtOAc/hexanes. Product isolated as a colorless oil.

Workup

  1. customReaction suspension
  2. customReaction
  3. extractionAqueous further extracted with EtOAc (2×25 mL)
  4. dry with materialCombined organics dried over MgSO4
  5. concentrationconcentrated
  6. custompurified on silica (40 g)
  7. washeluting with 10>40% EtOAc/hexanes
  8. customProduct isolated as a colorless oil

Sources & evidence

ORD record
ord-6e2f6a2df23743e3a6bd3337a6705800
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Reaction notes

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