Sodium borohydride → (3-Fluoro-2-methoxyphenyl)methanol

HRID 449832Notes

Reaction equation

HRID 449832 reaction equation
[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO.C(OCC)C>[F:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 125722773-Fluoro-2-methoxybenzaldehyde

Product 1

HCID 22505951(3-Fluoro-2-methoxyphenyl)methanolYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-fluoro-2-methoxy-benzaldehyde (3.41 g, 22.1 mmol) in methanol (20 mL) is slowly added portionwise sodium borohydride (1.00 g, 26.6 mmol). The reaction is stirred at room temperature under nitrogen overnight. The reaction is diluted with diethyl ether, washed with water twice, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 3.02 g (87%) of the title compound as a clear colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.09-6.92 (m, 3H), 4.65 (d, 2H), 3.97 (s, 3H), 2.14 (t, 1H, OH).

Workup

  1. washwashed with water twice
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e7b779f0ee9943a8bb1400187666e2ee
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

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