2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 1065185Notes

Reaction equation

HRID 1065185 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>[F:1][C:2]1[CH:8]=[C:7]([Br:9])[CH:6]=[CH:5][C:3]=1[NH2:4]

Participants

4

Reactant 2

HCID 95842-FluoroanilineHCID 67184N-bromobutanimide

Product 1

HCID 1230504-Bromo-2-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In methylene chloride (200 ml) was dissolved 2-fluoroaniline (51.0 g) and, under cooling at 0° C. and stirring N-bromosuccinimide (81.7 g) was added in small installments over a period of an hour. The mixture was further stirred for 20 minutes, after which it was washed with cold water and dried over anhydrous sodium sulfate. The methylene chloride layer was concentrated and the resultant oil was distilled under reduced pressure. By the above procedure, there was obtained 2-fluoro-4-bromoaniline as an oil boiling at 75°-80° C./0.3 mmHg.

Workup

  1. additionwas added in small installments over a period of an hour
  2. washafter which it was washed with cold water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe methylene chloride layer was concentrated
  5. distillationthe resultant oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-c45150150257448f805360b3547dceb9
Source dataset
uspto-grants-1982_05
Patent number
US04328367

Reaction notes

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