Hydrochloric Acid → 2-Fluoro-5-(trifluoromethyl)aniline

HRID 49954

Reaction equation

HRID 49954 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][C:9]=1[F:10])([O-])=O.Cl.C(=O)(O)[O-].[Na+].C(OCC)C>CO.[Fe]>[F:10][C:9]1[CH:8]=[CH:7][C:6]([C:11]([F:12])([F:13])[F:14])=[CH:5][C:4]=1[NH2:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineYield 82%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

Twenty grams of 3-nitro-4-fluorobenzotrifluoride was dissolved in 50 ml of methanol. An iron powder (16 g) was added and concentrated hydrochloric acid was added dropwise with stirring. The reaction mixture was stirred overnight, followed by addition of sodium bicarbonate for neutralization. Then diethyl ether was added, and the insolubles were filtered off with cerite. The ether phase was separated, dried and concentrated under reduced pressure, giving 14 g of the contemplated product (yield 82%).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationthe insolubles were filtered off with cerite
  3. customThe ether phase was separated
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67f0e5b6c7a5411682cf7addfc7c992c
Source dataset
uspto-grants-2004_03
Patent number
US06710062B1

Linked notes

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