C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[OH:29])[CH:24]=[O:25].O[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[O:36]1[CH2:37][CH2:38][N:33]([CH2:32][CH2:31][O:29][C:28]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][C:21]=2[Br:20])[CH2:34][CH2:35]1Triphenylphosphine (6.85 g) was added to a solution of 3-bromo-4-hydroxybenzaldehye (5 g) in tetrahydrofuran (40 ml), followed by addition of 2-hydroxyethylmorpholine (3.01 ml) and then the dropwise addition of diethylazodicarboxylate (4.11 ml). After 12 hours, the reaction was concentrated under reduced pressure, poured into 2N hydrochloric acid (200 ml) and extracted with ethyl acetate (2×150 ml). The aqueous layer was basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (2×150 ml). The organic layers were dried over magnesium sulfate and concentrated to afford 4.4 g (56%) of 4-morpholinoethoxy-3-bromobenzaldehyde as a reddish oil.
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