[C:1]1([C:7]2[S:8][C:9]([CH2:12]O)=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>C(Cl)Cl>[Br:34][CH2:12][C:9]1[S:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][CH:10]=1(2-phenylthiazol-5-yl)methanol (390 mg, 2.03 mmol) was dissolved in dry CH2Cl2 (10 mL) and cooled to 0° C. Triphenyl phosphine (800 mg, 3.05 mmol) was then added, followed by carbon tetrabromide (1.35 g, 4.07 mmol). The reaction mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction mixture was then concentrated under reduced pressure and the crude product was purified by column chromatography (silica 60-120 mesh, eluant 5% EtOAc in petroleum ether) to get 5-(bromomethyl)-2-phenylthiazole (250 mg, yield 48%) as light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.95-7.92 (m, 2H), 7.80 (s, 1H), 7.46-7.45 (m, 3H), 4.77 (s, 2H). MS (ESI) m/z: Calculated for C10H8BrNS: 254.95. found: 256.0 (M+H)+.
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