Boron tribromide → 2-Hydroxyxanthone

HRID 355426Notes

Reaction equation

HRID 355426 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[CH:8]=1>ClCCl>[OH:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:21])[C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 710342-Methoxyxanthone

Product 1

HCID 747082-HydroxyxanthoneYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (1.0M dichloromethane solution, 50 ml, 50 mmol) was added to a mixture of 2-methoxy-9H-xanthen-9-one (5.66 g, 25.0 mmol) and dichloromethane (50 ml), and the mixture was stirred for 3 hours. The reaction mixture was poured into ice water and the reaction product was extracted with chloroform. The extract was washed with water and saturated sodium chloride aqueous solution in that order, dried over anhydrous magnesium sulfate, and then concentrated under a reduced pressure to give the title compound (5.00 g, 23.6 mmol, 94%) as yellow crystals.

Workup

  1. extractionthe reaction product was extracted with chloroform
  2. washThe extract was washed with water and saturated sodium chloride aqueous solution in that order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-aaaf8e8072404f7482d874508a333cf3
Source dataset
uspto-grants-1998_11
Patent number
US05830902

Reaction notes

Loading…