Sodium borohydride → 1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol

HRID 1499830Notes

Reaction equation

HRID 1499830 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:5]([O:15][CH3:16])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10]>CO>[Br:3][C:4]1[C:5]([O:15][CH3:16])=[C:6]([CH:12]([OH:14])[CH3:13])[CH:7]=[C:8]([Cl:11])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866667591-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

Product 1

HCID 866668161-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanolYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydroborate (0.31 g, 8.1 mmol) was added to a mixture of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (1.5 g, 5.4 mmol) in methanol (25 mL) at 0° C. and the resultant reaction mixture was stirred at room temperature for 1 hour. The solvent was removed and the resulting residue was diluted with ethyl acetate, washed with sat. NaHCO3, water, brine, then dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with 0 to 40% EtOAc in hexanes, to give the desired product (0.30 g, 90%).

Workup

  1. customthe resultant reaction mixture
  2. customThe solvent was removed
  3. additionthe resulting residue was diluted with ethyl acetate
  4. washwashed with sat. NaHCO3, water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 0 to 40% EtOAc in hexanes

Sources & evidence

ORD record
ord-5a0fca772ec44f9eb4897d068a538b47
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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