Toluene → 5-Bromo-2-(3-(chloromethyl)phenoxy)pyrimidine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.S(Cl)([Cl:19])=O.C1(C)C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][Cl:19])[CH:10]=2)=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(3-(5-Bromopyrimidin-2-yloxy)phenyl)methanol (0.790 g, 2.81 mmol) in dichloromethane (9 mL) was cooled to 0° C. and treated dropwise with thionyl chloride (0.215 mL, 2.95 mmol). The reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. Toluene (5 mL) was added and the mixture was concentrated to give the title compound (0.815 g, 97% yield) as a semi-solid. MS (APCI) M+1=299.0.