2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 1439341Notes

Reaction equation

HRID 1439341 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-9405244e611c416e80ead9631dc1d3c9
Source dataset
uspto-grants-1977_11
Patent number
US04059434

Reaction notes

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