Potassium Carbonate → 1-Bromo-2-(2-benzyloxyeth-1-yloxy)-4-methoxybenzene

HRID 277503Notes

Reaction equation

[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]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A 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).

Workup

filtrationfiltered
customthe filtrate partitioned with EtOAc (1 L) and H2O (1 L)
washThe combined organic phases were washed with H2O (250 mL), brine (250 mL)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customto afford the crude product as a tan oil (142 g)
distillationdistilled (135° C./5 mm Hg)

Sources & evidence

ORD record: ord-c9fae7af73ea498a934dbd53bfabb915
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06355813B1

Reaction notes

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