Potassium Carbonate → 3-[4-(3,4-Difluoro-benzyloxy)-phenyl]-propionamide

HRID 2184357Notes

Reaction equation

HRID 2184357 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23]Br>CC(CC)=O.O>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([NH2:12])=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 16222514Phloretamide

Product 1

HCID 103795113-[4-(3,4-Difluoro-benzyloxy)-phenyl]-propionamideYield 41.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 106 mg (0.64 mmol) 3-(4-hydroxy-phenyl)-propionamide, 178 mg (1.29 mmol) potassium carbonate and 140 mg (0.68 mmol) 3,4-difluorobenzyl bromide in 5 ml ethyl methyl ketone is hold at 50° C. for 24 hours. The reaction mixture is cooled, diluted with water and extracted with diethyl ether. Crystallization from n-hexane yields 77 mg (41%) of a colorless solid. MS: m/e=291.3 (M+).

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with diethyl ether
  3. customCrystallization from n-hexane

Sources & evidence

ORD record
ord-29f34c6e629b400287a02cd3df9360c4
Source dataset
uspto-grants-2005_05
Patent number
US06900354B2

Reaction notes

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