Boron tribromide → 2-(4-Chloro-7-methylquinazolin-2-yl)-3-methylphenol

HRID 2062232Notes

Reaction equation

HRID 2062232 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[O:20]C)[N:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]2[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=2[OH:20])[N:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 580107904-Chloro-2-(2-methoxy-6-methyl-phenyl)-7-methyl-quinazoline

Product 1

HCID 1361214462-(4-Chloro-7-methylquinazolin-2-yl)-3-methylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chloro-2-(2-methoxy-6-methylphenyl)-7-methylquinazoline (669 mg, 2.24 mmol) in 7 mL CH2Cl2 was added dropwise 5 equivalents of a 1 M solution of BBr3 in CH2Cl2 at −78° C. The reaction was warmed to room temperature and was complete in 30 minutes. The reaction was quenched with a saturated aqueous NaHCO3 solution until the pH was neutral. The aqueous layer was extracted with CH2Cl2, dried over MgSO4, filtered, and concentrated to obtain 2-(4-chloro-7-methylquinazolin-2-yl)-3-methylphenol. LC/MS: m/z 285.1 (M+H)+ at 3.94 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe reaction was quenched with a saturated aqueous NaHCO3 solution until the pH
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8424b88027b04c9d8b25a93d50bd985d
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

Loading…