Acetonitrile → 2-[(3,4-Difluorobenzyl)-(2-hydroxyethyl)-amino]-1-(4-trifluoromethoxyphenyl)-ethanone
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9]CNCCO)[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)=[O:18].[C:30]([O-:33])([O-])=O.[K+].[K+].[C:36](#[N:38])C>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[CH2:9][N:38]([CH2:36][CH2:30][OH:33])[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)=[O:18]Participants
5
Procedure
To the 2-[2-(3,4-difluorophenyl)-ethylamino]-ethanol (0.5 g, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-(4-trifluoromethoxyphenyl)-ethanone (0.76 g, 2.7 mmol) and K2CO3 (0.44 g, 3.2 mmol). The reaction mixture was stirred at room temperature for 20 h, and concentrated in vacuo. Water was added to the concentrate, which was then extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (40% EtOAc/hexane) provided 2-[(3,4-difluorobenzyl)-(2-hydroxyethyl)-amino]-1-(4-trifluoromethoxyphenyl)-ethanone (0.8 g, 2.1 mmol).
Workup
- concentrationconcentrated in vacuo
- additionWater was added to the concentrate, which
- extractionwas then extracted with EtOAc
- washThe combined organic layers were washed with water and brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification by silica gel chromatography (40% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-a63694e3d34049fda8574452ed1499b2
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08236805B2
Reaction notes
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