Water → HCID 40044612, compound

HRID 1754964Notes

Reaction equation

HRID 1754964 reaction equation
C(N(CC)C(C)C)(C)C.Br[CH2:11][C:12]([O:14][CH3:15])=[O:13].[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][C:18]=1[C:24]([F:27])([F:26])[F:25].O>CN(C=O)C>[CH3:15][O:14][C:12](=[O:13])[CH2:11][NH:21][C:20]1[CH:22]=[CH:23][C:17]([Br:16])=[C:18]([C:24]([F:27])([F:25])[F:26])[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 60984Methyl bromoacetateHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 81531Diisopropylethylamine

Product 1

HCID 40044612HCID 40044612, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N,N-Diisopropylethylamine (1.22 ml, 7.00 mmol) and methyl bromoacetate (1.00 g, 6.54 mmol) were sequentially added to a solution of 4-bromo-3-(trifluoromethyl)aniline (1.40 g, 5.83 mmol) in DMF (10 ml), and the mixture was heated with stirring at 80° C. for 25 hours. The reaction mixture was cooled and water was then added, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was triturated with hexane:dichloromethane=9:1 to give (4-bromo-3-trifluoromethyl-phenylamino)-acetic acid methyl ester (1.22 g, 67%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was sequentially washed with water and saturated brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was triturated with hexane

Sources & evidence

ORD record
ord-e95a5bf121e24d65a3bdaba272ed158e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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