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

HRID 59274Notes

Reaction equation

HRID 59274 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-832e639c0de84943ba9acb6ba35acf26
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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