N-bromobutanimide → 6-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one

HRID 2180452Notes

Reaction equation

HRID 2180452 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:15])[CH2:8][C:9]([CH3:14])([CH3:13])[O:10]2)=[CH:5][CH:4]=1.[Br:16]N1C(=O)CCC1=O>CN(C)C=O>[Br:16][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:3]=1[O:2][CH3:1])[O:10][C:9]([CH3:13])([CH3:14])[CH2:8][C:7]2=[O:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6056607-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one2×

Product 1

HCID 134522776-Bromo-7-methoxy-2,2-dimethyl-chroman-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-methoxy-2,2-dimethyl-chroman-4-one (Compound 1, 5.81 g, 28.2 mmol) in anhydrous N,N-dimethylformamide (15 mL) under argon at 25° C. was added N-bromosuccinimide (5.02 g, 33.8 mmol). The mixture was stirred at ambient temperature for 12 h. The product was extracted with diethyl ether. The organic layers were washed with water, brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo and purified by column chromatography (silica gel, 5% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washThe organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe filtered solvent was concentrated in vacuo
  5. custompurified by column chromatography (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-812fe786c11a47178939303047a11002
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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