[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8].P(Br)(Br)[Br:17].O.C(OCC)(=O)C>COCCOC>[Br:17][CH2:14][C:11]1[CH:12]=[CH:13][C:2]([Cl:1])=[C:3]([CH:10]=1)[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8]
6.2 g of methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate was dissolved in 50 ml of ethylene glycol dimethyl ether, and 2.7 g of phosphorus tribromide was dropwise added to this solution at −20° C., followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction solution, extraction with ethyl acetate was carried out, followed by washing with an aqueous sodium hydrogencarbonate solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.1 g of methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate as white crystals.
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