Hydrochloric Acid → 3-(Difluoromethyl)-4-fluoroaniline
Reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[F:12].Cl>CO.[Fe]>[F:13][CH:2]([F:1])[C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[F:12])[NH2:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2-(difluoromethyl)-1-fluoro-4-nitrobenzene (1.2 g, 6.2 mmol) in methanol (20 mL) was added iron powder (4.8 g, 24.8 mmol) followed by conc. HCl (5 mL) dropwise. The reaction mass was stirred at RT for 1-2 h. The reaction mass was quenched in ice-water, basified with NaHCO3 and extracted with DCM. The organic layer was dried and concentrated to afford 0.800 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 5.25 (s, 2H), 6.66-6.73 (m, 2H), 6.86-7.04 (m, 2H).
Workup
- customThe reaction mass was quenched in ice-water
- extractionextracted with DCM
- customThe organic layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-182eba89c9924177b9238e987a6b84f0
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096545B2
Reaction notes
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