Cl.C(N(C1C=CC=CC=1)S(C1C=NC(N2C(=O)C(CC3C=NC=CC=3)=C(C)N2)=CC=1)(=O)=O)C.[CH3:34][O:35][CH2:36][C:37]1[CH:38]=[C:39]([CH2:43]O)[CH:40]=[CH:41][CH:42]=1.P(Br)(Br)[Br:46].CO>CCOCC>[Br:46][CH2:43][C:39]1[CH:40]=[CH:41][CH:42]=[C:37]([CH2:36][O:35][CH3:34])[CH:38]=1To a solution of 5.91 g (38.8 mmol) of 2 [3-(methoxymethyl)phenyl]methanol in 75 mL of Et2O are added dropwise, at 0° C., 9.1 mL (97.1 mmol) of phosphorus tribromide. The reaction mixture is allowed to warm slowly to room temperature and stirring is continued for 4 hours. The crude reaction mixture is then poured cautiously into a mixture of 100 g of ice and 100 mL of MeOH. After evaporating off the MeOH under reduced pressure, the aqueous phase is extracted with DCM (2×200 mL). The organic phases are combined, dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 20% EtOAc. 3.25 g of 1-(bromomethyl)-3-(methoxymethyl)benzene are thus obtained in the form of an oil.
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