Hydrochloric Acid → 3-(Difluoromethyl)-4-fluoroaniline

HRID 508763Notes

Reaction equation

HRID 508763 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

HCID 313Hydrochloric AcidHCID 217310702-(Difluoromethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 234450763-(Difluoromethyl)-4-fluoroanilineYield 80.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

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

  1. customThe reaction mass was quenched in ice-water
  2. extractionextracted with DCM
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-182eba89c9924177b9238e987a6b84f0
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

Loading…