Water → 2-Bromo-3-fluoroaniline
Reaction equation
[Br:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[F:11].[BH4-].[Na+].O>CO.Cl[Ni]Cl>[Br:1][C:2]1[C:3]([F:11])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-bromo-1-fluoro-3-nitrobenzene (1.0 g, 5.0 mmol) in CH3OH (50 L) was added NiCl2 (2.2 g 10 mmol) and NaBH4 (0.50 g 14 mmol) at 0° C. After the addition, the mixture was stirred for 5 min. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL×3). The organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give 2-bromo-3-fluoroaniline (600 mg, 70%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.02 (m, 1H), 6.55-6.49 (m, 1H), 4.22 (br s, 2H).
Workup
- additionAfter the addition
- extractionthe mixture was extracted with EtOAc (20 mL×3)
- dry with materialThe organic layers were dried over anhydrous Na2SO4
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-1b7a579a956c4b55b64826ff938fa3b8
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08623905B2
Reaction notes
Loading…