N-bromobutanimide → HCID 57467610, compound

HRID 423243Notes

Reaction equation

HRID 423243 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.[Br:13]N1C(=O)CCC1=O>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([F:11])[C:7]([OH:10])=[C:8]([Br:13])[CH:9]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 57467610HCID 57467610, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-fluoro-4-hydroxybenzoic acid methyl ester (1.0 g) in THF (10 mL) was added N-bromosuccinimide (1.26 g) under ice-cooling, and the mixture was stirred at room temperature for 2 hours The reaction solution was diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1, v/v) to give the title compound (1.16 g). (In the above, THF is tetrahydrofuran)

Workup

  1. temperaturecooling
  2. washwashed successively with saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-228cbbd811a94f878fcb2f5bc1593217
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

Loading…