4-Bromo-2-fluoroanisole → 3-Fluoro-4-methoxybenzonitrile

HRID 626129

Reaction equation

HRID 626129 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([F:10])[CH:3]=1.[C:11]([Cu])#[N:12]>CN(C=O)C.O>[F:10][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[C:11]#[N:12]

Participants

5

Reactant 2

HCID 753784-Bromo-2-fluoroanisoleHCID 178418546HCID 178418546, compound

Product 1

HCID 27745483-Fluoro-4-methoxybenzonitrileYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-2-fluoro-1-methoxybenzene (30.0 g, 146 mmol) and CuCN (15.6 g, 174 mmol) in dry DMF (45 mL) was stirred at 120° C. overnight. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The extract was washed with water and brine, dried, and concentrated to give 20.0 g (91% yield) of the product as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.44 (dd, J=8.8 Hz, 2.0 Hz, 1H), 7.36 (dd, J=10.8 Hz, 2.0 Hz, 1H), 7.02 (dd, J=8.8 Hz, 8.4 Hz, 1H), 3.96 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-06b96f53ce9c43e193786538c1a136cc
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Linked notes

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