[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:17][C:18]([CH3:23])([CH3:22])[C:19](Br)=[O:20].C(=O)C1C=CC=CC=1>C1COCC1>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:19](=[O:20])[C:18]([Br:17])([CH3:23])[CH3:22])=[CH:3][CH:4]=1)=[O:7]
A solution of 4-hydroxy benzaldehyde (6.1 g, 0.050 mol) and triethylamine (6.1 g, 0.060 mol) was stirred in THF (200 mL) in a round-bottom flask. Bromoisobutyryl bromide (13.6 g, 0.060 mol) was added slowly to the stirring benzaldehyde solution, and the reaction mixture was stirred at room temperature for five hours. The white precipitate that appeared was removed by filtration, and the solvent was removed by rotary evaporation. Purification by column chromatography (eluting with 12% EtOAc in hexane) provided the desired aldehyde (6.5 g) as a white solid. 1H NMR (CDCl3) δ=2.09 (s, 6H), 7.33 (d, J=7.2 Hz, 2H), 7.96 (d, J=7.99 Hz, 2H), 10.02 (s, 1H) ppm; 13C NMR (CDCl3) δ (ppm) 30.4, 55.3, 121.5, 131.3, 134.2, 155.3, 169.6, 175.7, 190.9 ppm.
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