N-bromobutanimide → 4-Bromo-2,5-difluoroaniline

HRID 1419645Notes

Reaction equation

HRID 1419645 reaction equation
[Br:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:11]=1[NH2:12]>ClCCl>[Br:1][C:15]1[C:14]([F:17])=[CH:13][C:11]([NH2:12])=[C:10]([F:9])[CH:16]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 677752,5-Difluoroaniline

Product 1

HCID 27732854-Bromo-2,5-difluoroaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-Bromosuccinimide (28.50 g, 0.160 mol) is added in small quantities over 1.5 hours to a stirred, cooled (-10° to 0° C.) solution of 2,5-difluoroaniline (20.00 g, 0.155 mol) in dry dichloromethane under dry nitrogen. This mixture is stirred at 0° C. for 2 hours (glc analysis revealing a complete reaction), and the red solution then washed with a large amount of water (×2) and dried (MgSO4). The solvent is removed in vacuo to afford a red solid with a yield of 32.19 g (100%).

Workup

  1. customa complete reaction), and the red solution
  2. washthen washed with a large amount of water (×2)
  3. dry with materialdried (MgSO4)
  4. customThe solvent is removed in vacuo
  5. customto afford a red solid with a yield of 32.19 g (100%)

Sources & evidence

ORD record
ord-1cb1bc0738c94d9fbb1fd2e8eb6a098f
Source dataset
uspto-grants-1999_03
Patent number
US05888421

Reaction notes

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