5-Bromo-4-fluoro-2-methylaniline → 5-Amino-2-fluoro-4-methylbenzonitrile

HRID 1497868Notes

Reaction equation

HRID 1497868 reaction equation
Br[C:2]1[C:3]([F:10])=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:11]([Cu])#[N:12]>CN1C(=O)CCC1.[Cu]I>[NH2:7][C:6]1[C:5]([CH3:9])=[CH:4][C:3]([F:10])=[C:2]([CH:8]=1)[C:11]#[N:12]

Participants

5

Reactant 2

HCID 27827865-Bromo-4-fluoro-2-methylanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 866774495-Amino-2-fluoro-4-methylbenzonitrileYield 36%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of 5-bromo-4-fluoro-2-methylaniline (2.04 g, 10.0 mmol), CuCN (889 mg, 10.0 mmol) and CuI (1.9 g, 10.0 mmol) in NMP was purged with N2 for 5 minutes and then sealed and heated at 195° C. for 30 minutes under microwave condition. The mixture was subjected to standard aqueous workup to give a residue which was purified by silica chromatography to yield 5-amino-2-fluoro-4-methylbenzonitrile (51) (540 mg, 36% yield). MS m/z 151.0 (M+1)+.

Workup

  1. customwas purged with N2 for 5 minutes
  2. customsealed
  3. customto give a residue which
  4. customwas purified by silica chromatography

Sources & evidence

ORD record
ord-c3a7388450ac4bc2b1bbbec2dfaf7471
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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