Acetic Acid → 6-bromo-7-methylquinazolin-4(3H)-one
Reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[NH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.CO.C(O)(=O)C.[Br:19]Br>>[Br:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH3:1])[N:9]=[CH:8][NH:7][C:6]2=[O:12]Participants
5
Procedure
7-methylquinazolin-4(3H)-one (14.56 g, 91 mmol) was added to methanol (70 ml, 91 mmol) and glacial acetic acid (70 ml, 1212 mmol). The mixture was stirred at RT for 5 min followed by the slow addition of bromine (9.3 mL, 182 mmol). The reaction was stirred at RT for 3 h. Volatiles were evaporated under reduced pressure and the resulting crude residue washed with aqueous sodium thiosulfate to remove excess bromine and HBr, then oven dried to give 6-bromo-7-methylquinazolin-4(3H)-one (18.35 g, 84% yield) as light yellow amorphous solid. MS (ESI, pos. ion) m/z: 239 [M+H]+
Workup
- stirringThe reaction was stirred at RT for 3 h
- customVolatiles were evaporated under reduced pressure
- washthe resulting crude residue washed with aqueous sodium thiosulfate
- customto remove excess bromine and HBr
- customoven dried
Sources & evidence
- ORD record
- ord-991dbaa4f839421393f41239d8578102
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557830B2
Reaction notes
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