Boron tribromide → 6-BROMO-4'-HYDROXYFLAVONE

HRID 215673Notes

Reaction equation

HRID 215673 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:24]>ClCCl>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)=[CH:10][C:9]2=[O:24]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 115372566-bromo-4'-methoxyflavone

Product 1

HCID 116453846-BROMO-4'-HYDROXYFLAVONE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (12 ml) that contained boron tribromide was slowly added to a dichloromethane solution (215 ml) that contained compound 15 (400 mg, 1.21 mmol) while stirring under cooling on ice, and the obtained mixture was then reacted. After completion of the reaction, purified water (100 ml) was added to the reaction solution, and the dichloromethane layer was extracted. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate/hexane (2/5) as an elution solvent, so as to obtain a product of interest, 6-bromo-4′-hydroxyflavone (compound 16). Yield: 50 mg (yield constant: 13.1%) 1H NMR (300 MHz, CDCl3) δ10.38 (s, 1H), 8.09 (s, 1H), 7.97-8.00 (m, 3H), 7.76 (d, J=9.0 Hz, 1H), 6.93-6.96 (m, 3H).

Workup

  1. temperatureunder cooling on ice
  2. customthe obtained mixture was then reacted
  3. customAfter completion of the reaction
  4. custompurified water (100 ml)
  5. additionwas added to the reaction solution
  6. extractionthe dichloromethane layer was extracted
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. distillationthe solvent was then distilled away under reduced pressure

Sources & evidence

ORD record
ord-e15c1c71cd694b0190755e567dcdb3df
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

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