Boron tribromide → HCID 178487429, compound

HRID 747868Notes

Reaction equation

HRID 747868 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:22])=[C:8]([C:14]3[CH:15]=[N:16][C:17]([O:20]C)=[CH:18][CH:19]=3)[C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:20][C:17]1[N:16]=[CH:15][C:14]([C:8]2[C:9](=[O:13])[O:10][C:11]3[C:6]([C:7]=2[CH3:22])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11551113HCID 11551113, compound

Product 1

HCID 178487429HCID 178487429, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-methoxy-3-(6-methoxy-pyridin-3-yl)-4-methyl-chromen-2-one in CH2Cl2 (5 mL) at room temperature was added BBr3 (1.0 N, 24.2 mmoL, 24 mL) dropwise. After addition, the reaction was slightly heated to reflux 4 hours. The reaction was quenched with ice sat. NaHCO3, extracted with 3×CH2Cl2, washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material. The crude material was re-crystallized in 2:1 hexanes:ethyl acetate to afford the title product as a pale reddish solid.

Workup

  1. additionAfter addition
  2. temperaturethe reaction was slightly heated
  3. temperatureto reflux 4 hours
  4. customThe reaction was quenched with ice sat. NaHCO3
  5. extractionextracted with 3×CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude material
  11. customThe crude material was re-crystallized in 2:1 hexanes

Sources & evidence

ORD record
ord-2927670821b245ab9f396caeeb172f37
Source dataset
uspto-grants-2008_07
Patent number
US07399767B2

Reaction notes

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