Water → 4-Bromo-2-fluoro-6-methylaniline

HRID 1372530Notes

Reaction equation

HRID 1372530 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[Br:10]N1C(=O)CCC1=O.O>CN(C)C=O.[Cl-].[Na+].O>[Br:10][C:7]1[CH:6]=[C:5]([CH3:9])[C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 141554112-Fluoro-6-methylaniline

Product 1

HCID 179726714-Bromo-2-fluoro-6-methylaniline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of crude 2-fluoro-6-methylaniline from step 3 (about 32 mmol) in anhydrous N,N-dimethylformamide (100 mL) was cooled in an ice bath, placed under a nitrogen atmosphere, treated with N-bromosuccinimide (5.7 g, 32 mmol), and then stirred at room temperature for 10 minutes. The reaction mixture was poured into a water solution of diluted brine and extracted with EtOAc. The organic extracts were washed with diluted brine three times, dried over MgSO4, filtered through a pad of silica, and concentrated under vacuum to afford 4-bromo-2-fluoro-6-methylaniline as a yellow foam.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with diluted brine three times
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through a pad of silica
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-703dcb10699d452fa7e3dc60c59b15ee
Source dataset
uspto-grants-2007_01
Patent number
US07157604B2

Reaction notes

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