4-Bromo-2-fluorotoluene → 3-Fluoro-4-methylbenzonitrile

HRID 1355608Notes

Reaction equation

HRID 1355608 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([F:12])[CH:6]=1>CN(C=O)C>[F:12][C:7]1[CH:6]=[C:5]([C:2]#[N:3])[CH:10]=[CH:9][C:8]=1[CH3:11]

Participants

4

Reactant 2

HCID 1710404-Bromo-2-fluorotolueneHCID 178418546HCID 178418546, compound

Product 1

HCID 5851403-Fluoro-4-methylbenzonitrileYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Copper(I) cyanide (Aldrich, 3.6 g, 40 mmol) was added to a solution of 4-bromo-2-fluorotoluene (Aldrich, 5 g, 27 mmol) in DMF (60 ml). The reaction mixture was heated at 150° C. for 11 hours. After cooling to room temperature, the mixture was partitioned between water and EtOAc (500 ml each). The organic layer was dried (MgSO4), and solvent was removed under vacuum to give the title compound (2.08, 58%). 1H NMR (CDCl3) δ 2.36 (s, 3H), 7.30 (m, 3H), 7.35 (d, 1H, J=8.1 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was partitioned between water and EtOAc (500 ml each)
  3. dry with materialThe organic layer was dried (MgSO4), and solvent
  4. customwas removed under vacuum

Sources & evidence

ORD record
ord-e1595deabe9f4e0290b1a2ee1860200b
Source dataset
uspto-grants-2003_07
Patent number
US06586405B2

Reaction notes

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