[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[CH2:17]([O:24][CH2:25][CH2:26]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:26][CH2:25][O:24][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1A 1 L three necked flask equipped with addition funnel was charged with 2-bromo -5-methoxyphenol (82.5 g, 0.4 mol) in DMF (600 mL) and treated with solid K2CO3 (61.75 g, 0.44 mol). The mixture was heated to 65° C. and benzyloxyethyl bromide (91.7 g, 0.42 mol) added dropwise over 30 minute period. After 2h the mixture was cooled to room temperature, filtered, and the filtrate partitioned with EtOAc (1 L) and H2O (1 L). The combined organic phases were washed with H2O (250 mL), brine (250 mL), dried (MgSO4) and concentrated in vacuo to afford the crude product as a tan oil (142 g). The oil was vacuum distilled (135° C./5 mm Hg) to afford 1-bromo-4-methoxy-2-[2-(phenylmethoxy)ethoxy]benzene as a colorless oil (125 g, 83%): 1H NMR δ7.45-7.25 (m, 6H), 6.55 (d, J=2.7 Hz, 1H), 6.4 (dd, J=8.6, 2.7 Hz, 1H), 4.7 (s, 2H), 4.2 (t, J=5.0 Hz, 2H), 3.9 (t, J=5.0 Hz, 2H), 3.75 (s, 3H).
Wird geladen…
