Boron tribromide → HCID 66917199, compound

HRID 238340Notes

Reaction equation

HRID 238340 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:14]1[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=1)=[CH:6][NH:7]2.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[CH:6][NH:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66917251HCID 66917251, compound

Product 1

HCID 66917199HCID 66917199, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

5-Fluoro-8-methoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one (1.0 g, 3.34 mmol) was suspended in dichloromethane (40 ml), and the suspension was cooled to −10° C. in a methanol-ice bath. A 1N boron tribromide (17 ml) was added thereto, and the resulting mixture was stirred at room temperature for 15 hours. Ice water and dichloromethane were added to the reaction mixture, and the resultant insoluble matter was collected by filtration. The substance remaining on the filter was washed with water, dried and purified by silica gel column chromatography (dichloromethane:methanol=20:1→8:1→4 ethyl acetate:methanol=4:1). The purified product was concentrated under reduced pressure and ethyl acetate was then added to crystallize the residue. The crystals were collected by filtration, washed with ethyl acetate, and dried to thereby obtain 360 mg of powdery pale gray 5-fluoro-8-hydroxy-3-(4-hydroxyphenyl)-1H-quinolin-4-one (yield: 40%).

Workup

  1. filtrationthe resultant insoluble matter was collected by filtration
  2. washwas washed with water
  3. customdried
  4. custompurified by silica gel column chromatography (dichloromethane:methanol=20:1→8:1→4 ethyl acetate:methanol=4:1)
  5. concentrationThe purified product was concentrated under reduced pressure and ethyl acetate
  6. additionwas then added
  7. customto crystallize the residue
  8. filtrationThe crystals were collected by filtration
  9. washwashed with ethyl acetate
  10. customdried

Sources & evidence

ORD record
ord-e4ee8923d3d04667a6043d35226251ad
Source dataset
uspto-grants-2014_02
Patent number
US08642619B2

Reaction notes

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