Hydrochloric Acid → N-(2,5-difluorophenyl)-3-hydroxypropionamide
Reaction equation
[Cl-].C([Al+]CC)C.[F:7][C:8]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=1[NH2:10].[C:16]1(=[O:20])[O:19][CH2:18][CH2:17]1.Cl>ClCCl>[F:7][C:8]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:9]=1[NH:10][C:18](=[O:19])[CH2:17][CH2:16][OH:20]Participants
Procedure
4 ml of a solution of diethylaluminum chloride (1M in hexane) is added dropwise at 0° C. to a solution of 0.519 g of 2,5-difluoroaniline in 10 ml of anhydrous dichloromethane. The reaction solution is stirred at room temperature for a further 20 minutes and subsequently cooled back to 0° C. A solution of 0.147 g of propiolactone in 8 ml of dichloromethane is added dropwise and the reaction mixture is stirred at room temperature over a further 2 hours. The reaction mixture is subsequently hydrolysed at 0° C. with 30 ml of 0.2M HCl and the phases are separated. The aqueous phase is re-extracted with 2×50 ml of dichloromethane and the combined organic phases are washed with 50 ml of water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.15 (1:1 EtOAc-heptane); Rt=2.62.
Workup
- temperaturesubsequently cooled back to 0° C
- stirringthe reaction mixture is stirred at room temperature over a further 2 hours
- customthe phases are separated
- extractionThe aqueous phase is re-extracted with 2×50 ml of dichloromethane
- washthe combined organic phases are washed with 50 ml of water
- dry with materialdried over sodium sulphate
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-25221e67b32741db9893bb3462d65590
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842688B2
Reaction notes
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