[C:1]([Br:5])(Br)(Br)Br.OC[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH2:16][OH:17])[CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:5][CH2:1][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([CH2:16][OH:17])[CH:9]=1Carbon tetrabromide (3.47 g) was added to a stirred solution of 1,3-dihydroxymethyl-5-methoxy-benzene (800 mg) in anhydrous dichloromethane (16 mL) under argon. After cooling the resulting solution at 0° C., a solution of triphenylphosphine (2.68 g) in anhydrous dichloromethane (16 mL) was added dropwise. The reaction mixture was stirred at room temperature for 20 h and then concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioPrep 90 g column, Si60 15-40 μm, eluted with methanol/dichloromethane, 4:96) to give 1-bromomethyl-3-hydroxymethyl-5-methoxy-benzene (420 mg):
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