Water → ethyl N-(4-fluorophenyl)glycine

HRID 1507634

Reaction equation

HRID 1507634 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH2:10][C:11](OCC)=O.[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].O.[CH3:23]N(C=O)C>>[CH2:10]([N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:23][C:16]([OH:17])=[O:19])[CH3:11]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 97314-FluoroanilineHCID 10340Sodium Carbonate

Product 1

HCID 61998283ethyl N-(4-fluorophenyl)glycine

Conditions

Temperature
70 °C

Procedure

Using the procedure described in WO 9857937 A2, to a solution of 13.56 g (122 mmole) p-fluoroaniline in DMF (100 mL) under nitrogen was added 23.5 g (141 mmol) of ethyl bromoacetate and 14.95 g (141 mmol) anhydrous sodium carbonate. The mixture was heated to 70° C. for 16 h and then cooled to room temperature. Water was added (500 mL) and the mixture stirred vigorously until a precipitate formed. The solid was filtered, washed with 100 mL water and dried to afford ethyl N-(4-fluorophenyl)glycine.

Workup

  1. temperaturecooled to room temperature
  2. customformed
  3. filtrationThe solid was filtered
  4. washwashed with 100 mL water
  5. customdried

Sources & evidence

ORD record
ord-e85fbe1affef462ab50755d2d5a46483
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Linked notes

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