N-bromobutanimide → Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester
Reaction equation
[Cl:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:13]N1C(=O)CCC1=O.N(/C(C)(C)C#N)=N\C(C)(C)C#N>C(#N)C>[Br:13][CH2:12][C:11]1[C:2]([Cl:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a solution of methyl 2-chloro-3-methylbenzoate (3.60 g, 19.4 mmol) in acetonitrile (60 mL) were added 1-bromopyrrolidine-2,5-dione (11.46 g, 64.3 mmol) and 2,2′-(E)-diazen-1,2-diylbis(2-methylpropanenitrile) (960 mg, 5.84 mmol), and the mixture was stirred at 90° C. for 26 hr. The reaction mixture was concentrated, the insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→5/95) to give the title compound (3.42 g, 66%) as a colorless oil.
Workup
- concentrationThe reaction mixture was concentrated
- filtrationthe insoluble material was filtered off
- concentrationthe filtrate was concentrated
- customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→5/95)
Sources & evidence
- ORD record
- ord-a90ddd25ca9a4d6887db6e34e629892e
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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