N-bromobutanimide → Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester

HRID 2190452Notes

Reaction equation

HRID 2190452 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

Reactant 3

HCID 67184N-bromobutanimideHCID 25067288Methyl 2-chloro-3-methylbenzoateHCID 178449902HCID 178449902, compound

Product 1

HCID 57386060Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl esterYield 66.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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)-diazene-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, insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→95/5) to give the title compound (3.42 g, 66%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationinsoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→95/5)

Sources & evidence

ORD record
ord-b5bdd2f4c3a242b9a7ea900765f9d072
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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