Dimethylformamide → 6-Amino-3-bromo-4-fluoro-2-methylbenzonitrile
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- customthe reaction liquid
- filtrationthe precipitated solid was collected by filtration
- washThe solid was washed with water
- customdried
Sources & evidence
- ORD record
- ord-dc698879c22a4075bb6d951fdb6285db
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737166B2
Reaction notes
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