Water → 4-Amino-3-bromo-2,5-difluorobenzonitrile
Reaction equation
[Br:1]Br.O.[NH2:4][C:5]1[C:12]([F:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([F:14])[CH:6]=1>C(O)(=O)C>[NH2:4][C:5]1[C:12]([F:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7]([F:14])[C:6]=1[Br:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of bromine (1.65 mL, 32 mmol), water (2 mL), and 4-amino-2,5-difluorobenzonitrile (5 g, 32 mmol) in acetic acid (50 mL) was stirred at RT for 16 h. The mixture was poured into ice cooled saturated sodium bicarbonate solution, causing a solid to separate out. The solid was filtered and washed with water. The solid was then dissolved in DCM, washed with water, dried over sodium sulfate, filtered, and concentrated to afford 7 g (92%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.18-7.21 (m, 1H), 4.80 (br. s, 2H).
Workup
- additionThe mixture was poured into ice cooled saturated sodium bicarbonate solution
- customto separate out
- filtrationThe solid was filtered
- washwashed with water
- dissolutionThe solid was then dissolved in DCM
- washwashed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-462d0895a7ef4bb5b090541c1dc150e0
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378104B2
Reaction notes
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