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

HRID 1499695Notes

Reaction equation

HRID 1499695 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)ethanol

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 (from Example 11, Step 1) (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 (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 (0.30 g, 90%)

Sources & evidence

ORD record
ord-fcbab94b01c642d6a31594a7484a4637
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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