Chloroacetyl chloride → 2-chloro-N-(1-(3-fluorophenyl)-2-hydroxyethyl)acetamide
Reaction equation
C(N(CC)CC)C.[NH2:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:10][OH:11].[Cl:19][CH2:20][C:21](Cl)=[O:22]>C1COCC1>[Cl:19][CH2:20][C:21]([NH:8][CH:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:10][OH:11])=[O:22]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In step 2-2, triethylamine (8.15 mL, 58.6 mmol) in a single portion was added to a solution of 2-amino-2-(3-fluorophenyl)ethanol (7.57 g, 48.8 mmol) in THF cooled to 0° C. and chloroacetyl chloride (5.08 mL, 58.6 mmol) was added drop-wise. The mixture was cooled to 0° C. and stirred for 1 hour. The reaction mixture was quenched with water and the organic phase was washed with 0.5 N HCl, saturated NaHCO3, brine, and dried over MgSO4. The organic phase was concentrated and purified with flash chromatography (50% EtOAc/hexanes) to yield 2-chloro-N-(1-(3-fluorophenyl)-2-hydroxyethyl)acetamide (2-2) as a yellow solid.
Workup
- temperatureThe mixture was cooled to 0° C.
- customThe reaction mixture was quenched with water
- washthe organic phase was washed with 0.5 N HCl, saturated NaHCO3, brine
- dry with materialdried over MgSO4
- concentrationThe organic phase was concentrated
- custompurified with flash chromatography (50% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-7db8fa5fe2d34573bce64a93c3d657ef
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507488B2
Reaction notes
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