Water → Ethyl 3-bromo-2-oxoheptanoate
Reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:13]Br.O.C(Cl)Cl>CC(O)=O>[Br:13][CH:8]([CH2:9][CH2:10][CH2:11][CH3:12])[C:2](=[O:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cold solution of ethyl 2-oxoheptanoate (2 g, 11.62 mmol) in AcOH (20 mL), was added Br2 (596 μL, 11.62 mmol). The mixture was stirred 20 minutes at 0° C., then the mixture was allowed to warm to rt. After the mixture was stirred for 3 h, water and CH2Cl2 were added. The organic phase was separated, dried (MgSO4), and evaporated to give crude ethyl 3-bromo-2-oxoheptanoate as a dark oil; 1H NMR (400 MHz, CDCl3) δ 5.05-5.01 (m, 1 H), 4.45-4.20 (m, 2 H), 2.18-1.94 (m, 2 H), 1.74-1.57 (m, 2 H), 1.48-1.17 (m, 5 H), 0.95-0.82 (m, 3 H). This compound was used without purification for the preparation of compounds of the invention such as 1-(4-chlorophenyl)-2-(2-chlorophenyl)-N-(1-piperidinyl)-5-butyl-1H-imidazole-4-carboxamide hydrochloride (Table entry 20).
Workup
- temperatureto warm to rt
- stirringAfter the mixture was stirred for 3 h
- customThe organic phase was separated
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-f3ecb0009f0047b8b6f0c10862cb0762
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960601B2
Reaction notes
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