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 insoluble material was filtered off from the reaction mixture, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→95/5), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (3.42 g, 66%) as a colorless oil.
Workup
- filtrationThe insoluble material was filtered off from the reaction mixture
- concentrationthe filtrate was concentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→95/5)
- additionthe fractions containing the object product
- concentrationwere concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f5b37c05a78e40198342dc6670e158b2
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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