Methanol → 4-Bromo-2-fluoro-6-methoxybenzonitrile

HRID 1502073Notes

Reaction equation

HRID 1502073 reaction equation
[CH3:1][OH:2].[Br:3][C:4]1[CH:11]=[C:10](F)[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.[Cl-].[Na+].O>[Br:3][C:4]1[CH:11]=[C:10]([O:2][CH3:1])[C:7]([C:8]#[N:9])=[C:6]([F:13])[CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To methanol (0.28 mL, 6.9 mmol) and 4-bromo-2,6-difluorobenzonitrile (1500 mg, 6.88 mmol) in THF (34 mL) was added NaHMDS (6.88 mL, 1.0 M in THF, 6.88 mmol) at 0° C. The reaction mixture was stirred at rt overnight, and diluted with brine, extracted with EtOAc. The organic layer was dried, and evaporated. The crude product was purified by column chromatography (0-30% EtOAc/Hex) to give 4-bromo-2-fluoro-6-methoxybenzonitrile.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was dried
  3. customevaporated
  4. customThe crude product was purified by column chromatography (0-30% EtOAc/Hex)

Sources & evidence

ORD record
ord-034cdd84f10f43d5b1f09f17125f0487
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

Loading…