[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11]([CH:13]1[O:15][CH2:14]1)Br.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH:13]2[CH2:14][O:15]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]
A mixture of 5-bromo-2-hydroxybenzaldehyde (10 g, 50 mmol), epibromohydrin (13.6 g, 100 mmol) and K2CO3 (10.3 g, 75 mmol) in DMF (50 ml) was heated at 60° C. for 2 h. The mixture was cooled to ambient temperature and water and EtOAc was added. The phases were separated and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the title compound (12.3 g). MS m/z (rel. intensity, 70 eV) 256 (M+, 41), 201 (77), 200 (bp), 199 (84), 63 (60).
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