Boron tribromide → HCID 69267868, compound

HRID 215679Notes

Reaction equation

HRID 215679 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:26]>ClCCl>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:24])[CH3:25])=[CH:19][CH:18]=1)=[CH:11][C:10]2=[O:26]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 25096969HCID 25096969, compound

Product 1

HCID 69267868HCID 69267868, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A dichloromethane solution (5 ml) that contained boron tribromide was slowly added to a dichloromethane solution (50 ml) that contained compound 25 (200 mg, 0.68 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 chloroform/methanol (20/1) as an elution solvent, so as to obtain a product of interest, 6-hydroxy-4′-dimethylaminoflavone (compound 27). Yield: 25 mg (yield constant: 13.1%) 1H NMR (300 MHz, DMSO-d6) δ 9.94 (s, 1H), 7.90 (d, J=9.0 Hz, 2H), 7.30 (m, 1H), 7.19-7.22 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 6.73 (s, 1H), 3.03 (s, 6H).

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-d6caddb62b7e42b989566445532ee750
Source dataset
uspto-grants-2012_06
Patent number
US08192717B2

Reaction notes

Loading…