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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 576334Generated: October 31, 2026

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

https://huagongshe.com/reaction/576334

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 numberUS09034921B2
Source datasetuspto-grants-2015_05
ORD IDord-30339ba797054e6bba0d5dcbfcb86040
Source noteuspto-grants-2015_05