3-Bromo-4-fluorobenzaldehyde → 2-Fluoro-5-formylbenzonitrile

HRID 1466735Notes

Reaction equation

HRID 1466735 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[C:11]([Cu])#[N:12]>CN1C(=O)CCC1>[F:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 1736043-Bromo-4-fluorobenzaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 27695822-Fluoro-5-formylbenzonitrileYield 107.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To NMP (40 ml) were added 3-bromo-4-fluorobenzaldehyde (10 g, 0.05 mol) and CuCN (5 g, 0.055 mol). The resulting mixture was heated at 170 for 24 h until the reaction finished (monitored by TLC), and cooled to 80, 10 g of celite was added and stirred for 1 h at this temperature. The reaction mixture then was cooled to room temperature, and partitioned between ethyl acetate (250 ml) and water (125 ml), the organic phase was washed with water and brine, dried, filtered, and concentrated to give the crude. Then the crude was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=4:1) to afford target compound (8 g, 100%) as a light yellow solid.

Workup

  1. temperatureThe resulting mixture was heated at 170 for 24 h until the reaction finished (monitored by TLC)
  2. temperaturecooled to 80, 10 g of celite
  3. additionwas added
  4. custompartitioned between ethyl acetate (250 ml) and water (125 ml)
  5. washthe organic phase was washed with water and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude
  10. customThen the crude was purified by column chromatography on silica gel (Petroleum ether:Ethyl Acetate=4:1)

Sources & evidence

ORD record
ord-919069b4e75b45b1b091e2370b116aed
Source dataset
uspto-grants-2015_04
Patent number
US08999985B2

Reaction notes

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