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

HRID 30317Notes

Reaction equation

HRID 30317 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 eq, available from Aldrich Chemical Company) in methanol at −10° C. under nitrogen atmosphere is added NaBH4 (7.515 g, 2.7 equiv.) portionwise. The solution is allowed to warm to room temperature and after 30 minutes the reaction solvent is removed under reduced pressure and replaced with dichloromethane. This solution is poured onto ice water and further extracted with dichloromethane. The organic fractions are collected and dried (MgSO4) and the solvent removed under reduced pressure to give the title compound as an oil (9.794 g, 87%). MW 156.16; C8H9FO2; 1H NMR (CDCl3): 2.58 (m, 1H), 3.81 (s, 3H), 4.63 (d, 2H, 6.3 Hz), 6.78 (dd, 1H, 8.9 Hz and 4.3 Hz), 6.94 (td, 1H, 8.5 Hz and 3.1 Hz), 7.04 (dd, 1H, 8.7 Hz and 3.1 Hz).

Workup

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

Sources & evidence

ORD record
ord-38bfed12353e491ea158194cd30ce5de
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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