Water → 4-Bromo-2-fluoro-3-(trifluoromethyl)aniline

HRID 341737

Reaction equation

HRID 341737 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12].O>CN(C)C=O>[Br:1][C:15]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([F:9])[C:16]=1[C:17]([F:18])([F:19])[F:20]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 1455693-Amino-2-fluorobenzotrifluoride

Product 1

HCID 536697144-Bromo-2-fluoro-3-(trifluoromethyl)anilineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (24.9 g) in N,N-dimethyl formamide was added to a solution of 2-fluoro-3-trifluoromethylaniline (25 g) in dimethyl formamide. The mixture was stirred for four and a half hours. It was poured into water and the oil was separated. The aqueous layers was extracted with ether and the combined organic layers were washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give 4-bromo-2-fluoro-3-trifluoromethylaniline (27.44 g) as an orange oil, b.p. 88°-94° C./4 mbar.

Workup

  1. customthe oil was separated
  2. extractionThe aqueous layers was extracted with ether
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. distillationthe residue was distilled

Sources & evidence

ORD record
ord-631dc0120bfa4282a8aa156e9f50f95d
Source dataset
uspto-grants-1999_01
Patent number
US05856274

Linked notes

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