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

HRID 899076Notes

Reaction equation

HRID 899076 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+]>CO>[F:11][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH2:5][OH:6])[CH:7]=1

Participants

4

Reactant 2

HCID 27349435-Fluoro-2-methoxybenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22014996(5-Fluoro-2-methoxyphenyl)methanolYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-Methoxy-5-fluorobenzaldehyde (11.093 g, 1 equiv.-available from Aldrich Chemical Company) in methanol at −10° C. under nitrogen atmosphere was added NaBH4 (7.515 g, 2.7 equiv.) portionwise. The solution was allowed to warm to room temperature and after 30 minutes the reaction solvent was removed under reduced pressure and replaced with dichloromethane. This solution was poured onto ice water and further extracted with dichloromethane. The organic fractions were collected and dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as an oil (9.794 g, 87%). 1H NMR (300 MHz, CDCl3): δ 2.58 (m, 1H), 3.81 (s, 3H), 4.63 (d, 2H, J=6.3 Hz), 6.78 (dd, 1H, J=8.9 and 4.3 Hz), 6.94 (td, 1H, J=8.5 and 3.1 Hz), 7.04 (dd, 1H, J=8.7 and 3.1 Hz).

Workup

  1. customwas removed under reduced pressure
  2. additionThis solution was poured onto ice water
  3. extractionfurther extracted with dichloromethane
  4. customThe organic fractions were collected
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-359d0170fb414cac9da5d727bdc79bfe
Source dataset
uspto-grants-2008_04
Patent number
US07354920B2

Reaction notes

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