Boron tribromide → 2-(6-Bromo-4-chloroquinazolin-2-yl)phenol

HRID 2062209Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline (393 mg, 1:12 mmol) was dissolved in CH2Cl2 (3 mL), and the flask was flushed with N2. After cooling the reaction mixture to −78° C., 1 M BBr3 in CH2Cl2 (3.37 mL, 3.37 mmol) was added dropwise, then the reaction was slowly warmed to room temperature and stirred-for 2 h. After quenching the mixture with saturated aqueous NaHCO3 (1×), it was transferred into a separatory funnel with CH2Cl2. The organic layer was washed with H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-5% EtOAc and CH2Cl2:hexanes (1:1) gave 2-(6-bromo-4-chloroquinazolin-2-yl)phenol (229 mg, 61%). LC/MS: m/z 335.30 (M+H)+ at 4.18 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

customthe flask was flushed with N2
temperaturethe reaction was slowly warmed to room temperature and stirred-for 2 h
customAfter quenching the mixture with saturated aqueous NaHCO3 (1×), it
customwas transferred into a separatory funnel with CH2Cl2
washThe organic layer was washed with H2O (2×)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification via silica gel chromatography

Sources & evidence

ORD record: ord-38f681347514455b9022c6ba28a0cdbc
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283354B2

Reaction notes

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