[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O-:12].[Na+].CO>CO.C(Cl)Cl.O>[Br:1][C:2]1[CH:9]=[C:8]([O:12][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]To a solution of 2-bromo-4-fluorobenzaldehyde (50 g, 246 mmol), in MeOH (500 mL) in a 15° C. water bath was added a 25% solution of NaOMe/MeOH (88 mL). The mixture was stirred at r.t. for 1 hour followed by 2 hours at reflux. The solid was filtered and the filtrate was concentrated to dryness to give a second crop of solid. Both crops were taken up in CH2Cl2/H2O. After washing with H2O, the organic phase was dried (MgSO4), filtered, and evaporated to give an off-white solid (52.2 g).
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