Water → HCID 69592463, compound

HRID 1836999Notes

Reaction equation

HRID 1836999 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-0dcf9bc8b36c4b57b148b7b80b1102a7
Source dataset
uspto-grants-2004_08
Patent number
US06780858B2

Reaction notes

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