2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 2419971Notes

Reaction equation

HRID 2419971 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12]>C(Cl)Cl>[Br:1][C:15]1[CH:14]=[CH:13][C:11]([NH2:12])=[C:10]([F:9])[CH:16]=1

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 67184N-bromobutanimide

Product 1

HCID 1230504-Bromo-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

160 Parts of solid N-bromosuccinimide were added in portions over a 2-hour period to a solution of 100 parts of 2-fluoroaniline in 400 parts of methylene chloride cooled to 0°. 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 with anhydrous sodium sulfate and evaporated under 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline, nD25 : 1.5885.

Workup

  1. temperaturecooled to 0°
  2. washthe dark red mixture was washed four times
  3. dry with materialThe red organic phase was dried with anhydrous sodium sulfate
  4. customevaporated under 300 mm. Hg to 164 parts of brown, oily 4-bromo-2-fluoroaniline

Sources & evidence

ORD record
ord-2de13e6d805749b4898cc4c5bb0f27c6
Source dataset
uspto-grants-1978_08
Patent number
US04108628

Reaction notes

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