Boron tribromide → HCID 58030373, compound

HRID 2360108Notes

Reaction equation

HRID 2360108 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19]C)=[CH:8][O:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])=[CH:8][O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66629240HCID 66629240, compound

Product 1

HCID 58030373HCID 58030373, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-80 °C

Procedure

To a stirred solution of 7-hydroxy-3-(2-methoxyphenyl)-8-methyl-4H-chromen-4-one (5 gm, 17.7 mmol) in dry CH2Cl2 (50 ml) at −80° C. was added BBr3 (3.4 ml in DCM, 35.4 mmol). The reaction mixture was then stirred for 1 hour at −80° C. and 12 hours at room temperature. The reaction was then quenched with ice-cooled water. The reaction mixture was then extracted with CH2Cl2 and the organic layer was separated, washed with brine, dried over Na2SO4, and evaporated. The residue was purified by silica gel column chromatography using hexane-chloroform as the eluent to give 7-hydroxy-3-(2-hydroxy-phenyl)-8-methyl-chromen-4-one (3.5 gm, 72%) as white solid.

Workup

  1. customThe reaction was then quenched with ice-
  2. temperaturecooled water
  3. extractionThe reaction mixture was then extracted with CH2Cl2
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-54278cd7dc53475c9aaaf510a09d5fd9
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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