2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 1112579Notes

Reaction equation

HRID 1112579 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:9]N1C(=O)CCC1=O>C(Cl)Cl>[Br:9][C:7]1[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 67184N-bromobutanimide

Product 1

HCID 1230504-Bromo-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 parts of 2-fluoroaniline in 400 parts of methylene chloride was cooled to 0°, and 160 parts of solid N-bromosuccinimide was added in portions over a 2-hour period. After stirring for 20 minutes, the dark red mixture was washed four times; 200 parts of cold water were used for each washing. The red organic phase was dried over anhydrous sodium sulfate and evaporated at a reduced pressure 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline, nD25 : 1.5885.

Workup

  1. washthe dark red mixture was washed four times
  2. dry with materialThe red organic phase was dried over anhydrous sodium sulfate
  3. customevaporated at a reduced pressure 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline

Sources & evidence

ORD record
ord-be63138b839442268776102a63158ee6
Source dataset
uspto-grants-1978_10
Patent number
US04123252

Reaction notes

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