Bromine → 3-Bromoacetyl-2,5-difluorobenzonitrile
Reaction equation
[C:1]([C:4]1[C:5]([F:13])=[C:6]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:7]#[N:8])(=[O:3])[CH3:2].[Br:14]Br>C(Cl)(Cl)Cl>[Br:14][CH2:2][C:1]([C:4]1[C:5]([F:13])=[C:6]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:7]#[N:8])=[O:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a stirred mixture of 6.85 g of 3-acetyl-2,5-difluorobenzonitrile and 220 mL of CHCl3 heated at reflux is added dropwise over 75 minutes a solution of 2.1 mL of Br2 in 50 mL of CHCl3. The mixture is boiled for another 15 minutes, cooled to 25° C., washed sequentially with saturated NaHCO3 and H2O (200 mL each), dried with Na2SO4 and stripped in vacuo to 10.26 g of brown oil. The oil which contains 78% of 3-bromoacetyl-2,5-difluorobenzonitrile by NMR analysis is satisfactory for the next step.
Workup
- temperatureheated
- temperatureat reflux
- washwashed sequentially with saturated NaHCO3 and H2O (200 mL each)
- dry with materialdried with Na2SO4
Sources & evidence
- ORD record
- ord-711a5d62b9fd4f5899b610671c8498c8
- Source dataset
- uspto-grants-1989_09
- Patent number
- US04863959
Reaction notes
Loading…