Ethanol → (3-Bromo-5-methoxyphenyl)methanol

HRID 2069076Notes

Reaction equation

HRID 2069076 reaction equation
[BH4-].[Na+].C(O)C.C1COCC1.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1)[CH:15]=[O:16]>C(OCC)(=O)C>[Br:11][C:12]1[CH:13]=[C:14]([CH2:15][OH:16])[CH:17]=[C:18]([O:20][CH3:21])[CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 106086983-Bromo-5-methoxybenzaldehyde

Product 1

HCID 10608788(3-Bromo-5-methoxyphenyl)methanolYield 99.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

NaBH4 (3.85 g; WAKO) was added to an ethanol (80 mL) and THF (20 mL) mixture solution of 3-bromo-5-methoxybenzaldehyde (22 g) with ice cooling and the resulting mixture was stirred at room temperature for 3 hours. The resulting mixture was poured into ice water (300 mL) and ethyl acetate (300 mL) was added thereto to extract the mixture with and the organic layer was washed with saturated aqueous sodium bicarbonate solution (300 mL) and then dried. The solvent was evaporated under reduced pressure to give the title compound (22.05 g).

Workup

  1. additionwas added
  2. extractionto extract the mixture with and the organic layer
  3. washwas washed with saturated aqueous sodium bicarbonate solution (300 mL)
  4. customdried
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d21a6e2210e746d6a1f88bff71c28453
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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