N-bromobutanimide → Methyl 2-(bromomethyl)-4-chlorobenzoate

HRID 447855Notes

Reaction equation

HRID 447855 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH3:20])[CH:11]=1.C(=O)([O-])O.[Na+]>C(OC(C)(C)C)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Cl:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH2:20][Br:1])[CH:11]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 22349978Methyl 4-Chloro-2-methylbenzoate

Product 1

HCID 20814722Methyl 2-(bromomethyl)-4-chlorobenzoateYield 83.9%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 10908tert-Butyl acetateSolvent

Procedure

(Step 2) A solution of N-bromosuccinimide (6.33 g), 2,2′-azobis(isobutyronitrile) (0.27 g) and methyl 4-chloro-2-methylbenzoate obtained in Step 1 (5.05 g) in t-butyl acetate (80 ml) was stirred overnight at 90° C. The mixture was allowed to cool to room temperature, poured into aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=0:1-3:17) to give methyl 4-chloro-2-bromomethylbenzoate (6.05 g) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=0:1-3:17)

Sources & evidence

ORD record
ord-29c54f7c1c4c4bca929b1bd3788b3c61
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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