Chlorosuccinimide → Methyl 3-amino-6-bromo-5-chloro-2-methylbenzoate

HRID 887788Notes

Reaction equation

HRID 887788 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([Br:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:14]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([Br:12])=[C:10]([Cl:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 59145915Methyl 3-amino-6-bromo-2-methylbenzoate

Product 1

HCID 59145910Methyl 3-amino-6-bromo-5-chloro-2-methylbenzoateYield 96%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-amino-6-bromo-2-methylbenzoate (960 mg, 3.93 mmol) in acetonitrile (40 mL) was added N-chlorosuccinimide (525 mg, 3.93 mmol) under ice-cooling, and the mixture was stirred at 60° C. for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→30/70) to give the title compound (1.05 g, yield 96%).

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→30/70)

Sources & evidence

ORD record
ord-72ebd1ccd32d4327b0c57f09b9feccb9
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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