Boron tribromide → 4-(6-Hydroxy-4-methylquinazolin-2-yl)benzoic acid

HRID 1627651Notes

Reaction equation

HRID 1627651 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1)[N:7]=[C:6]2[CH3:22].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:13]1[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:20][CH:21]=1)[N:7]=[C:6]2[CH3:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 679750294-(6-Methoxy-4-methylquinazolin-2-yl)benzoic acid

Product 1

HCID 574071584-(6-Hydroxy-4-methylquinazolin-2-yl)benzoic acidYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(6-methoxy-4-methylquinazolin-2-yl)benzoic acid (180 mg, 0.612 mmol) in anhydrous DCM (10 mL) was added BBr3 (0.29 mL, 3.05 mmol, d=2.64 g/mL) dropwise at 0° C. The resulting mixture was stirred at 25° C. for 16 hours. The reaction mixture was quenched with H2O (30 mL), then extracted with DCM (20 mL×3). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the crude product. The crude product was washed with MeOH (10 mL) to give Compound V-2 (130 mg, yield 76%). 1H NMR (DMSO-d6 400 MHz): δ 13.06 (brs, 1H), 10.46 (brs, 1H), 8.60 (d, J=8.4 Hz, 2H), 8.09 (d, J=8.4 Hz, 2H), 7.95 (d, J=9.2 Hz, 1H), 7.56 (dd, J=8.8, 2.4 Hz, 1H), 7.41 (d, J=2.4 Hz, 1H), 2.90 (s, 3H). MS (ESI): m/z 280.9 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with H2O (30 mL)
  2. extractionextracted with DCM (20 mL×3)
  3. washThe combined organic layers were washed with brine (20 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc1e0dd0216f45868c8c9f8eeff56fb1
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

Loading…