Dimethylformamide → 6-Amino-3-bromo-4-fluoro-2-methylbenzonitrile

HRID 17550Notes

Reaction equation

HRID 17550 reaction equation
[Br:1]N1C(=O)CCC1=O.CN(C)C=O.[NH2:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([CH3:24])[C:16]=1[C:17]#[N:18]>O>[NH2:14][C:15]1[C:16]([C:17]#[N:18])=[C:19]([CH3:24])[C:20]([Br:1])=[C:21]([F:23])[CH:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 450790392-Amino-4-fluoro-6-methylbenzonitrile

Product 1

HCID 541071796-Amino-3-bromo-4-fluoro-2-methylbenzonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Bromosuccinimide (16.6 g, 93.3 mmol) was gradually added to an N,N-dimethylformamide (250 ml) solution of 2-amino-4-fluoro-6-methylbenzonitrile (I-264) (14.0 g, 93.3 mmol). After stirring for 6 hours, the reaction liquid was poured into water with ice (750 ml), the precipitated solid was collected by filtration. The solid was washed with water, then dried to obtain the entitled compound (20.2 g, 95%) as a gray solid.

Workup

  1. customthe reaction liquid
  2. filtrationthe precipitated solid was collected by filtration
  3. washThe solid was washed with water
  4. customdried

Sources & evidence

ORD record
ord-dc698879c22a4075bb6d951fdb6285db
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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