Hydrochloric Acid → 5-(Difluoromethyl)-2-fluoroaniline

HRID 1898321Notes

Reaction equation

HRID 1898321 reaction equation
[F:1][CH:2]([F:13])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1.Cl.C(=O)(O)[O-].[Na+]>CO.O.[Fe]>[F:13][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[C:5]([CH:4]=1)[NH2:10]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 203877754-(Difluoromethyl)-1-fluoro-2-nitrobenzene

Product 1

HCID 675035275-(Difluoromethyl)-2-fluoroanilineYield 89.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(difluoromethyl)-1-fluoro-2-nitrobenzene (0.200 g, 1.04 mmol) in methanol (10 mL) was added iron powder (0.500 g, 8.92 mmol). The reaction mass was cooled at 0° C. followed by drop-wise addition of conc. HCl (3.0 mL). The reaction mass was stirred at RT for 1 h. The reaction mass was diluted with water and basified with sodium bicarbonate, extracted with DCM. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.150 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 5.44 (s, 2H), 6.67 (m, 1H), 6.86 (s, 1H), 6.93 (d, J=8.1 Hz, 1H), 7.05-7.12 (m, 1H); MS [M+H]+: 160.13.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b945e62a4fc4433af968a87d3fe26cc
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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