N-bromobutanimide → 2-Bromo-4-fluoro-5-methoxyaniline

HRID 495437Notes

Reaction equation

HRID 495437 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH3:10].[Br:11]N1C(=O)CCC1=O>ClCCl>[Br:11][C:7]1[C:5]([NH2:6])=[CH:4][C:3]([O:9][CH3:10])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27745334-Fluoro-3-methoxyaniline

Product 1

HCID 223266662-Bromo-4-fluoro-5-methoxyanilineYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-3-methoxyaniline (9.87 g, 70 mmol) and N-bromosuccinimide (12.46 g, 70 mmol) in dichloromethane (150 ml) was stirred at room temperature for 1 h (exothermic). The reaction mixture was evaporated in vacuo to give a dark slurry which was chromatographed on silica gel (˜350 g) using a gradient elution 20-50% ethyl acetate in hexane to give the title compound as a brown solid (12.70 g, 82%).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customto give a dark slurry which
  3. customwas chromatographed on silica gel (˜350 g)
  4. washa gradient elution 20-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-788b66aaf20d4a71bdf5ea34b6ee0070
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

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