Dimethylformamide → 4-Bromo-3-fluoro-2-methoxy-5-methylaniline

HRID 17300Notes

Reaction equation

HRID 17300 reaction equation
CN(C)C=O.[Br:6]N1C(=O)CCC1=O.[F:14][C:15]1[C:16]([O:23][CH3:24])=[C:17]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[NH2:18]>[Cl-].[Na+].O>[Br:6][C:21]1[C:20]([CH3:22])=[CH:19][C:17]([NH2:18])=[C:16]([O:23][CH3:24])[C:15]=1[F:14]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 67184N-bromobutanimideHCID 451220523-Fluoro-2-methoxy-5-methylaniline

Product 1

HCID 860974514-Bromo-3-fluoro-2-methoxy-5-methylanilineYield 81.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

With cooling with ice, an N,N-dimethylformamide (10 ml) solution of N-bromosuccinimide (1.84 g, 10.2 mmol) was dropwise added to an N,N-dimethylformamide (20 ml) solution of 3-fluoro-2-methoxy-5-methylaniline (I-26) (1.55 g, 10.0 mmol), taking 25 minutes, followed by stirring for 18 hours with gradually heating up to room temperature. Saturated brine was added to the reaction liquid, followed by extraction twice with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the resulting residue was subjected to column chromatography, and the eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure to obtain the entitled compound (1.91 g, 81%) as a brown oily substance.

Workup

  1. temperatureWith cooling with ice
  2. extractionfollowed by extraction twice with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. concentrationthe eluate with n-hexane:ethyl acetate (4:1) was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6573c56e8ad840fab2ca1fc2954a6f24
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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