Methanol → 7-Hydroxyflavone

HRID 2301345Notes

Reaction equation

HRID 2301345 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 4662687-Methoxyflavone

Product 1

HCID 52818947-HydroxyflavoneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.4 mmol) of compound 7-methoxy-2-phenyl-chromen-4-one obtained in Example 2 was dissolved in methylenechloride, and 2.0 molar equivalents of BBr3 was added thereto. The mixture was stirred for 1 hour. Methanol was added to the mixture, and then solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylenechloride/methanol=5/95, v/v) to give the title compound in a yield of 64%.

Workup

  1. customsolvent was removed by distillation under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (eluent: methylenechloride/methanol=5/95, v/v)

Sources & evidence

ORD record
ord-9dc41ea52f97412d947902986a95a9ff
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

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