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

HRID 1857095Notes

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 2 h 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 δ 7.45-7.25 (m, 6 H), 6.55 (d, J=2.7 Hz, 1 H), 6.4 (dd, J=8.6, 2.7 Hz, 1 H), 4.7 (s, 2 H), 4.2 (t, J=5.0 Hz, 2 H), 3.9 (t, J=5.0 Hz, 2 H), 3.75 (s, 3 H).

Workup

temperatureAfter 2 h the mixture was cooled to room temperature
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-6b17b4363fd14f56bcf4da6b9dca22c4
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143907

Reaction notes

Loading…