Boron tribromide → 2-(3-hydroxyphenyl)quinazolin-4(3H)-one

HRID 61528Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

To 2-(3-methoxyphenyl)quinazolin-4(3H)-one (11.6 g, 45.98 mmole) was added of CH2Cl2 (120 mL) and the mixture was cooled to −78° C. Then, a 1 M solution of BBr3 in CH2Cl2 (60 mL, 60.0 mmol) was added drop wise and the reaction was stirred at −78° C. for 1 h and then ambient temperature for 3 h. The reaction was re-cooled to −78° C. and cautiously quenched with MeOH (20 mL). The ice bath was removed and the system allowed to stir at ambient temperature for 0.5 h. The pH was adjusted to 7 with 10% w/w NaHCO3 solution. The solid was filtered, washed with ether, dried and then azeotroped from toluene (3 X) and dried under high vacuum overnight to give 2-(3-hydroxyphenyl)quinazolin-4(3H)-one. (11.0 g, mmol, 100%).

Workup

waitambient temperature for 3 h
temperatureThe reaction was re-cooled to −78° C.
customcautiously quenched with MeOH (20 mL)
customThe ice bath was removed
stirringto stir at ambient temperature for 0.5 h
filtrationThe solid was filtered
washwashed with ether
customdried
customazeotroped from toluene (3 X)
customdried under high vacuum overnight

Sources & evidence

ORD record: ord-ec8ecfd06b184fdd881c4efedc514ac4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440961B2

Reaction notes

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