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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 604741Generated: October 25, 2026

Boron trifluoride etherate → 1-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzene

https://huagongshe.com/reaction/604741

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantSodium CarbonateHCID 10340—
ReactantTriethylsilaneHCID 12052—
Reactant(5-Bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanoneHCID 67069096—
SolventAcetonitrile chloroformHCID 22555007—
Product1-Bromo-4-chloro-5-(4-ethoxybenzyl)-2-methoxybenzeneHCID 67069105102.5%

Reaction Steps

Then, Et3SiH (1.62 mL, 10.1 mmol) and BF3.Et2O (0.772 mL, 6.09 mmol) were added sequentially to a chloroform-acetonitrile (1:1; 16 mL) solution of (5-bromo-2-chloro-6-methoxyphenyl)(4-ethoxyphenyl)methanone (1.50 g, 4.06 mmol) at −5° C. The reaction mixture was warmed to room temperature and stirred for 16 hours. After the reaction mixture was added with a saturated sodium carbonate aqueous solution and extracted with chloroform, the organic layer was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain a colorless oily title compound (1.48 g, 99%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07910619B2
Source datasetuspto-grants-2011_03
ORD IDord-b52cbb492d474c209d8263430bfad604
Source noteuspto-grants-2011_03