3,5-Difluorobenzonitrile → 3-Fluoro-5-methoxybenzonitrile

HRID 2114676Notes

Reaction equation

HRID 2114676 reaction equation
[CH3:1][O-:2].[Na+].[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11](F)[CH:12]=1)[C:8]#[N:9]>CO.CN(C)C=O.CCOCC>[F:4][C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([O:2][CH3:1])[CH:12]=1)[C:8]#[N:9]

Participants

6

Reactant 2

HCID 5872043,5-DifluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 106306843-Fluoro-5-methoxybenzonitrile

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (1.50 ml of a 4.5M solution in methanol, 7.10 mmol) was added dropwise to a stirred solution of 3,5-difluorobenzonitrile (1.00 g, 7.10 mmol) in N,N-dimethylformamide (36 ml) at 0° C. under nitrogen. The reaction was allowed to warm to room temperature and stirred for 14 hours. The reaction was diluted with ether (40 ml), washed with water (3×100 ml) and brine (100 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5, by volume) to provide the title compound (418 mg) as a yellow oil.

Workup

  1. washwashed with water (3×100 ml) and brine (100 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel eluting with cyclohexane:ethyl acetate (95:5, by volume)

Sources & evidence

ORD record
ord-cb8e465f99a84be590fe5d409208795f
Source dataset
uspto-grants-2008_10
Patent number
US07435728B2

Reaction notes

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