4-Bromo-2-fluoroaniline → 4-Amino-3-fluorobenzonitrile
Reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[C:10]([Cu])#[N:11]>CN1C(=O)CCC1>[NH2:6][C:5]1[CH:7]=[CH:8][C:2]([C:10]#[N:11])=[CH:3][C:4]=1[F:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
50 g (0.26 mol) of 4-bromo-2-fluoroaniline and 30 g (0.34 mol) of CuCN were dissolved in 130 cm3 of NMP and the solution was refluxed with a mantle heater for 2 hours. The reaction solution was cooled to room temperature. 42 cm3 of EDA was added to the cooled solution and the solution was poured into 300 cm3 of ice water. The resulting mixture was extracted with chloroform and washed with an aqueous EDA solution and water. The chloroform was distilled off the washed mixture. The distillation residue was dissolved in ether and washed with water to remove the NMP. The residue was distilled in a vacuum (b.p. 165° C./23 mmHg) to yield 28 g (0.21 mol) of 4-amino-3-fluorobenzonitrile. It was necessary to perform the distillation under an elevated degree of vacuum since the product was extremely sublimable and the crystals adhered to the output of the distillation tube and clogged the tube.
Workup
- temperaturethe solution was refluxed with a mantle heater for 2 hours
- addition42 cm3 of EDA was added to the cooled solution
- extractionThe resulting mixture was extracted with chloroform
- washwashed with an aqueous EDA solution and water
- distillationThe chloroform was distilled off the washed mixture
- dissolutionThe distillation residue was dissolved in ether
- washwashed with water
- customto remove the NMP
- distillationThe residue was distilled in a vacuum (b.p. 165° C./23 mmHg)
Sources & evidence
- ORD record
- ord-cf33db391ba64eb2b1e6fdbba93f60e3
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05238599
Reaction notes
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