Allyl bromide → 1-(Allyloxy)-2-bromo-5-chloro-4-(4-ethoxybenzyl)benzene

HRID 1410295Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)[C:5]([Cl:18])=[CH:4][C:3]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]=[CH2:28]>CC(C)=O>[CH2:28]([O:19][C:3]1[CH:4]=[C:5]([Cl:18])[C:6]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH3:17])=[CH:13][CH:14]=2)=[CH:7][C:2]=1[Br:1])[CH:27]=[CH2:26]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 2-Bromo-5-chloro-4-(4-ethoxybenzyl)phenol (7, 55 mmol) in acetone (180 mL) were added potassium carbonate (15.2 g, 110 mmol) and allyl bromide (7 mL, 83 mmol) and heated at 65° C. for 3 h. The insoluble material was removed by filter and the filtrate was evaporated under reduced pressure. The crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes) to yield the title compound (21 g, 52 mmol, 95%) as colorless oil.

Workup

customThe insoluble material was removed
filtrationby filter
customthe filtrate was evaporated under reduced pressure
customThe crude residue was purified on Biotage® purification apparatus (silica gel, 3 to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-92f298d08a9e4a669cd2a312da931b70
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921412B2

Reaction notes

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