Chloroacetyl chloride → HCID 58155316, compound
Reaction equation
[NH2:1][C:2]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[F:15])([CH:5]1[CH2:7][CH2:6]1)[CH2:3][OH:4].C(=O)([O-])O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([F:15])=[C:8]([C:2]([NH:1][C:23](=[O:24])[CH2:22][Cl:21])([CH:5]2[CH2:7][CH2:6]2)[CH2:3][OH:4])[CH:13]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(RS)-2-Amino-2-(5-bromo-2-fluoro-phenyl)-2-cyclopropyl-ethanol (2.27 g, 8 mmol) was dissolved in a mixture of dichloromethane (85 ml) and a saturated aqueous solution of sodium hydrogen-carbonate (85 ml). The biphasic mixture was then treated with a solution of chloroacetylchloride (0.69 ml, 8.7 mmol) in dichloromethane. The reaction mixture was stirred at room temperature and the progress of the transformation checked by chromatography. After completion, the reaction mixture was diluted with dichloromethane, the organic layer separated and washed with water, then dried over sodium sulfate and evaporated. The (RS)-N-[1-(5-bromo-2-fluoro-phenyl)-1-cyclopropyl-2-hydroxy-ethyl]-2-chloro-acetamide was obtained as a yellow oil (2.73 g, 94.0% of theory). Mass (calculated) C13H14BrClFNO2 [350.614]; (found) [M+H]+=350, [M+2-H]+=352, [M+4-H]+=354.