N-bromobutanimide → Methyl 3-amino-6-bromo-5-fluoro-2-methylbenzoate

HRID 887780Notes

Reaction equation

HRID 887780 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Br:14]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([Br:14])=[C:10]([F:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53419617Methyl 3-amino-5-fluoro-2-methylbenzoate

Product 1

HCID 59145869Methyl 3-amino-6-bromo-5-fluoro-2-methylbenzoateYield 89.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-amino-5-fluoro-2-methylbenzoate (1.37 g, 7.48 mmol) in acetonitrile (57 mL) was added N-bromosuccinimide (1.01 g, 5.66 mmol) under ice-cooling, and the mixture was stirred for 2 hr. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (1.33 g, yield 68%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

Sources & evidence

ORD record
ord-dcc2122e14cb48eb99102b147426f582
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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