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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2206707Generated: November 3, 2026

Boron trifluoride etherate → 1-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzene

https://huagongshe.com/reaction/2206707

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantTriethylsilaneHCID 12052—
Reactant(5-Bromo-2-chloro-3-methoxyphenyl)(4-ethylphenyl)methanoneHCID 71110682—
SolventDichloromethaneHCID 6344—
Product1-(4-Ethylbenzyl)-5-bromo-2-chloro-3-methoxybenzeneHCID 7107705156.1%

Reaction Steps

To a solution of compound 61 (4.45 g, 12.6 mmol) in CH2Cl2 (80 mL) was added dropwise triethylsilane (6.00 mL, 37.8 mmol) and boron trifluoride diethyl etherate (4.67 mL, 37.8 mmol) at 0° C. under an atmosphere of nitrogen. After being stirred for 5 hours at room temperature, the mixture was quenched with aq. saturated K2CO3 solution (30 mL) and extracted with EtOAc. 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 afford the product 62 (2.40 g, 56%) as colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09371303B2
Source datasetuspto-grants-2016_06
ORD IDord-fe5f7788b6044e809141d00f28f15c92
Source noteuspto-grants-2016_06