Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 576401Generated: October 30, 2026

N,N-Diethylaniline → 2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenol

https://huagongshe.com/reaction/576401

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN,N-DiethylanilineHCID 7061—
Reactant1-(Allyloxy)-5-bromo-2-chloro-3-(4-methoxybenzyl)benzeneHCID 86714081—
Product2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenolHCID 8671408091%

Reaction Conditions

Temperature200 °C

Reaction Steps

The mixture of bromide 184 (2.52 g, 6.85 mmol) in N,N-diethylaniline (8 mL) was stirred at 200° C. for 45 hours. The mixture was cooled to rt and extracted with EtOAc/aq. 1N HCl solution (100 mL/100 mL). The organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired product 185 (2.3 g, 91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09034921B2
Source datasetuspto-grants-2015_05
ORD IDord-ce36f20688f54bcd84b71ddb0f5bde40
Source noteuspto-grants-2015_05