5-Fluoro-2-methoxybenzaldehyde → (5-Fluoro-2-methoxyphenyl)methanol

HRID 736031Notes

Reaction equation

HRID 736031 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH:11]=1)[CH:9]=[O:10]>CCO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([O:12][CH3:13])=[C:8]([CH2:9][OH:10])[CH:11]=1

Participants

4

Reactant 2

HCID 27349435-Fluoro-2-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22014996(5-Fluoro-2-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add Sodium borohydride (540 mg, 13.95 mmol) in portions to a solution of 5-Fluoro-2-methoxy-benzaldehyde (2.15 g, 13.94 mmol) in absolute EtOH (20 ml) and stir at room temperature. After 1 h, evaporate the solvent, dilute the residue in CH2Cl2 and treat with aqueous 3M HCl. Separate the phases, wash the organic one twice with H2O, dry over Na2SO4 and concentrate at vacuum to obtain pure (5-Fluoro-2-methoxy-phenyl)-methanol as white solid. Add aqueous concentrated HBr (15 ml) to a solution of (5-Fluoro-2-methoxy-phenyl)-methanol (1.9 g, 12.17 mmol) in CHCl3 (10 ml) and stir at room temperature. After 1 h, separate the phases, wash the aqueous one with CH2Cl2, combine organic phases, wash with H2O, dry over Na2SO4 and concentrate at vacuum to obtain a residue. Purify the residue by column chromatography on silica gel eluting with hexane to afford 2-Bromomethyl-4-fluoro-1-methoxy-benzene as white solid. 1H-NMR (CDCl3, 200 Mz): δ 7.06 (dd, J=3.0 and 8.6 Hz, 1H), 6.98 (m, 1H), 6.81 (dd, J=4.4 and 9.0 Hz, 1H), 4.50 (s, 2H), 3.87 (s, 3H).

Workup

  1. customevaporate the solvent
  2. additiondilute the residue in CH2Cl2
  3. additiontreat with aqueous 3M HCl
  4. customSeparate the phases
  5. washwash the organic one twice with H2O
  6. dry with materialdry over Na2SO4
  7. concentrationconcentrate at vacuum

Sources & evidence

ORD record
ord-20695852b1af473a955abac512c692b4
Source dataset
uspto-grants-2009_09
Patent number
US07595315B2

Reaction notes

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