Boron tribromide → HCID 58030370, compound

HRID 2360107Notes

Reaction equation

HRID 2360107 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19]C)[C:5]2=[O:21].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH:7]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[C:5]2=[O:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58913587HCID 58913587, compound

Product 1

HCID 58030370HCID 58030370, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-80 °C

Procedure

To a stirred solution of 6-chloro-7-hydroxy-3-(2-methoxyphenyl)-4H-chromen-4-one (2.5 gm, 8.3 mmol) in dry CH2Cl2 (25 ml) at −80° C. was added BBr3 (1.6 ml in DCM, 16.6 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 6-chloro-7-hydroxy-3-(2-hydroxy-phenyl)-chromen-4-one (1.4 gm, 60%) 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-3aaed97687b44e788fe46a2c8be35310
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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