Benzoyl Peroxide → 6-(Bromomethyl)-4-chloroquinazoline

HRID 901327Notes

Reaction equation

HRID 901327 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 9402174-chloro-6-methylquinazoline

Product 1

HCID 219419376-(Bromomethyl)-4-chloroquinazolineYield 47.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

A flask containing 4-Chloro-6-methylquinazoline (0.91 g, 5.09 mmol), NBS (0.95 g, 5.35 mmol), benzoyl peroxide 70% (0.09 g, 0.2545 mmol) and carbon tetrachloride (25 mL) is refluxed at 80° C. for 20 h. The solution is cooled to RT, filtered and concentrated. Purification by flash chromatography (7.5% EtOAc/hexanes) yields the title compound as a white solid (0.62 g, 2.42 mmol). 1H NMR (CDCl3, 300 MHz) 9.06(s, 1H), 8.25(s, 1H), 8.07(d, 1H), 8.00(d, 1H), 4.67(s, 2H).

Workup

  1. temperatureThe solution is cooled to RT
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customPurification by flash chromatography (7.5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d79dfa200cc24a62a93dd4575eb9c82f
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

Loading…