2-Fluoroaniline → 4-Bromo-2-fluoroaniline

HRID 1741548Notes

Reaction equation

HRID 1741548 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]>ClCCl>[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-fluoroanilineYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (160.4 g, 0.90 mol) was added in small portions to a stirred, cooled solution of 2-fluoroaniline (100.0 g, 0.90 mol) in dry dichloromethane (400 ml). The stirred mixture was allowed to warm to 0° C. over 45 min, washed with water and dried (MgSO4). The solvent was removed in vacuo to yield a red solid (180 g) which was steam distilled to give a colourless solid.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aee0714d05c0443db3849da4d623bd6c
Source dataset
uspto-grants-1994_08
Patent number
US05334327

Reaction notes

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