Water → HCID 69592463, compound

HRID 858320Notes

Reaction equation

HRID 858320 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Br[CH2:14][C:15]([O:17]CC)=[O:16].[C:20]([O-:23])([O-])=[O:21].[K+].[K+].O.[CH3:27][N:28]([CH:30]=O)[CH3:29]>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12].[CH2:30]([N:28]([C:29]1[CH:7]=[CH:8][C:2]([Cl:1])=[C:3]([C:9]([F:12])([F:10])[F:11])[CH:4]=1)[CH2:27][C:20]([OH:23])=[O:21])[CH3:14]

Participants

7

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 675744-Chloro-3-(trifluoromethyl)aniline

Product 2

HCID 22137855HCID 22137855, compoundHCID 69592463HCID 69592463, compoundYield 9%

Conditions

Temperature
70 °C

Procedure

The required N-(4-chloro-3-trifluoromethylphenyl)glycine was prepared as follows. A mixture of 4-chloro-3-trifluoromethylaniline (1.369 g, 7 mmol), ethyl bromoacetate (1.55 mL, 14 mmol), K2CO3 (2.764 g, 20 mmol) in DMF (40 mL) was heated at 70° C. overnight. It was then poured into water and extracted with EtOAc. The organic layer was separated, washed with brine, dried with anhydrous Na2SO4, concentrated by rotary evaporation and purified by flash chromatography on silica gel with a gradient elution of 20–40% EtOAc/hexanes to afford ethyl N-(4-chloro-3-trifluoromethylphenyl)glycine as a white solid (0.180 g, 9%).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. custompurified by flash chromatography on silica gel with a gradient elution of 20–40% EtOAc/hexanes

Sources & evidence

ORD record
ord-fa83b47ee1184040ad560e34655412a3
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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