2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 1763212Notes

Reaction equation

HRID 1763212 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 yield 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

Sources & evidence

ORD record
ord-b4a288cadc0e4d48afb730dda1b40e45
Source dataset
uspto-grants-1978_09
Patent number
US04111681

Reaction notes

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