4'-Bromo-3-chloropropiophenone → 4-Bromo-alpha-(2-chloroethyl)benzenemethanol

HRID 515477Notes

Reaction equation

HRID 515477 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH2:11][CH2:12][Cl:13])=[CH:6][CH:5]=1>O1CCCC1>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:14])[CH2:11][CH2:12][Cl:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 957904'-Bromo-3-chloropropiophenoneHCID 4311764Sodium borohydride

Product 1

HCID 108006384-Bromo-alpha-(2-chloroethyl)benzenemethanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium borohydride (3.8 g, 100 mmol) in tetrahydrofuran (100 mL) was added a solution of 1-(4-bromo-phenyl)-3-chloro-propan-1-one (25 g, 100 mmol) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 2 hours. The reaction mixture was concentrated to about 50 mL under reduced pressure and diluted with water. Extractive workup was performed with ethyl acetate and the extracts were dried over anhydrous sodium sulfate. After concentration, the residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate=3/1 as an eluant) to yield 1-(4-bromo-phenyl)-3-chloro-propan-1-ol (25 g, 100 mmol, 100%) as yellow oil.

Workup

  1. concentrationThe reaction mixture was concentrated to about 50 mL under reduced pressure
  2. additiondiluted with water
  3. dry with materialthe extracts were dried over anhydrous sodium sulfate
  4. concentrationAfter concentration
  5. customthe residue was purified by flash column chromatography on silica gel (hexane/ethyl acetate=3/1 as an eluant)

Sources & evidence

ORD record
ord-f8cca119a8b44ea48e10615c8ca24783
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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