Water → 1196093-39-6

HRID 2192362Notes

Reaction equation

HRID 2192362 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Br:16][CH2:17][C:18](Br)=[O:19].O>ClCCl>[Br:16][CH2:17][C:18]([NH:4][C:3]1[C:2]([F:1])=[CH:8][CH:7]=[CH:6][C:5]=1[F:9])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 796472,6-Difluoroaniline

Product 1

HCID 606517911196093-39-6

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,6-difluoroaniline (1.12 g) and potassium carbonate (1.8 g) in 50 mL dichloromethane was added bromoacetyl bromide (1.5 mL) and the mixture was stirred at room temperature for 17 h. Water was added and the mixture stirred for several hours then the phases were separated on a hydrophobic frit and the organic layer was evaporated. The crude product was purified by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane to give the sub-titled compound (0.92 g) as a white solid.

Workup

  1. stirringthe mixture stirred for several hours
  2. customthe phases were separated on a hydrophobic frit
  3. customthe organic layer was evaporated
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with 0-100% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-8890ce025c234df4bdf6c63ff5005ddb
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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