Methanol → 4H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-

HRID 884672Notes

Reaction equation

HRID 884672 reaction equation
O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11].B(Br)(Br)Br.CO>ClCCl>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[O:11][C:4]3[C:3]([C:8](=[O:20])[CH:9]=2)=[CH:2][CH:7]=[CH:6][CH:5]=3)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 777921,3-Propanedione, 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-

Product 1

HCID 777934H-1-Benzopyran-4-one, 2-(4-methoxyphenyl)-Yield 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione (200 mg, 0.74 mmol) in dichloromethane (15 mL) was added BBr3 (185 mg, 0.74 mmol, 1M solution in dichloromethane) slowly at 0° C., and then stirred for overnight at rt. Then MeOH was added at 0° C. to quench the unreacted BBr3. The organic layer was washed with water, dried and concentrated to give a crude product, which was purified by column chromatography using 30% EtOAc in hexane to afford 50 mg (26%) of 2-(4-methoxy-phenyl)-4H-chromen-4-one. MS (ES) m/z: 253.08 (M+1), and 149.00.

Workup

  1. customto quench the unreacted BBr3
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-f60093ee07ef48a8b03dd66e222acbc8
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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