2-Fluoro-4-nitro-1-(trifluoromethyl)benzene → 4-Amino-2-fluorobenzotrifluoride

HRID 1917901Notes

Reaction equation

HRID 1917901 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]>CO.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[C:11]([F:13])([F:14])[F:12]

Participants

4

Reactant 1

HCID 149414112-Fluoro-4-nitro-1-(trifluoromethyl)benzene

Product 1

HCID 27359144-Amino-2-fluorobenzotrifluoride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a round bottomed flask, 2-fluoro-4-nitro-1-trifluoromethyl-benzene (1.00 g, 4.78 mmol) was dissolved in 10 mL of methanol. To this solution was added 10% palladium on carbon (100 mg) and the solution was stirred overnight at room temperature under hydrogen (1 atm). The solution was filtered and concentrated to afford 3-fluoro-4-trifluoromethyl-phenylamine. 1H NMR (300 MHz, DMSO-d6) δ 7.3 (m, 1H), 6.6 (d, 2H), 6.2 (s, 2H)

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d55aa128e99043fea9ecfea37806c927
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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