Boron tribromide → HCID 22490938, compound

HRID 2180483Notes

Reaction equation

HRID 2180483 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[O:8][C:7]([CH3:15])([CH3:14])[CH:6]=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7]([CH3:15])([CH3:14])[CH:6]=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22491026HCID 22491026, compound2×

Product 1

HCID 22490938HCID 22490938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-bromo-7-methoxy-2,2-dimethyl-4-phenyl-2H-chromene (Compound 52, 992 mg, 3.22 mmol) in dichloromethane (20 mL) under argon at 0° C. was added boron tribromide (1M in dichloromethane, 3.8 mL, 3.8 mmol). The mixture was stirred at 0° C. for 1 h, then quenched with ice. The product was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over Na2SO4. The filtered solvent was concentrated in vacuo and purified by column chromatography (silica gel, 5% ethyl acetate in hexane) to produce the title compound as a white solid.

Workup

  1. customquenched with ice
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe filtered solvent was concentrated in vacuo
  6. custompurified by column chromatography (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-dbe9bfa3309a42938981dba384a01314
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

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