4-Bromo-2,6-difluorobenzonitrile → 4-Bromo-2-fluoro-6-methoxybenzonitrile

HRID 515191Notes

Reaction equation

HRID 515191 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.[CH3:12][O-:13].[Na+]>O1CCCC1>[Br:1][C:2]1[CH:9]=[C:8]([O:13][CH3:12])[C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 27569164-Bromo-2,6-difluorobenzonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrileYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2,6-difluoro-benzonitrile (15.0 g, 68.8 mmol) in tetrahydrofuran (150 ml) is added sodium methoxide (4.5 g, 82.6 mmol) at room temperature and the mixture is stirred for 16 h. The reaction mixture is concentrated under reduced pressure and the resulting solid is purified by column chromatography (silica gel, 5% ethyl acetate/hexane) to obtain 4-bromo-2-fluoro-6-methoxy-benzonitrile (8.5 g, 36.9 mmol, 53%).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe resulting solid is purified by column chromatography (silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-79b6a41160804129bd0f086abf770979
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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