Boron tribromide → HCID 136372378, compound

HRID 1469211Notes

Reaction equation

HRID 1469211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[C:11]([O:19]C)[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[C:11]([OH:19])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 135443732HCID 135443732, compound

Product 1

HCID 136372378HCID 136372378, compoundYield 85%

Procedure

2-(4-Fluorophenyl)-8-methoxyquinazolin-4(3H)-one (460 mg, 1.70 mmol) was dissolved under argon in boron tribromide solution (1M solution in tetrahydrofuran; 5.11 ml, 5.11 mmol) and stirred under reflux conditions for 4 h. After cooling to room temperature, the solvent was removed under reduced pressure, and the residue was taken up in aqueous sodium hydroxide solution (10 ml) and stirred at room temperature for a further 3 h. Subsequently, the reaction solution was neutralized with dilute aqueous hydrochloric acid (1M). Filtration with suction and thorough drying gave 2-(4-fluorophenyl)-8-hydroxyquinazolin-4(3H)-one (370 mg, 85% of theory) as a colorless solid. 1H NMR (400 MHz, d6-DMSO δ, ppm) 12.49 (br. s, 1H, NH), 9.65 (br. s, 1H, OH), 8.49 (m, 2H), 7.67 (dd, 1H), 7.38 (m 2H), 7.34 (d, 1H), 7.23 (dd, 1H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. stirringstirred at room temperature for a further 3 h
  3. filtrationFiltration with suction
  4. customthorough drying

Sources & evidence

ORD record
ord-35dc491f8ca64245ad1e55f6692cd655
Source dataset
uspto-grants-2015_04
Patent number
US09006265B2

Reaction notes

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