Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1469174Generated: November 1, 2026

Boron trifluoride etherate → 5-Bromo-2-chloro-3-(4-methoxybenzyl)thiophene

https://huagongshe.com/reaction/1469174

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantPotassium CarbonateHCID 11430—
ReactantTriethylsilaneHCID 12052—
Reactant(5-Bromo-2-chlorothiophen-3-yl)(4-methoxyphenyl)methanoneHCID 66692728—
SolventAcetonitrile methylene chlorideHCID 21877088—
Product5-Bromo-2-chloro-3-(4-methoxybenzyl)thiopheneHCID 6669545482%

Reaction Steps

To a solution of methanone 2 (2.68 g, 8.08 mmol) in CH2Cl2/CH3CN (20 mL/20 mL) were added triethylsilane (3.9 mL, 24.2 mmol) and boron trifluoride diethyl etherate (3.1 mL, 24.2 mmol) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 hours. To the mixture was added aq. saturated K2CO3 solution (50 mL) slowly and extracted with EtOAc (50 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 3 (2.09 g, 82%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006187B2
Source datasetuspto-grants-2015_04
ORD IDord-b09cc84ade394b96bf97c174a4fab68e
Source noteuspto-grants-2015_04