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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 909776Generated: November 1, 2026

Boron trifluoride etherate → 2-(5-Bromo-2-chlorobenzyl)-1-benzothiophene

https://huagongshe.com/reaction/909776

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantTriethylsilaneHCID 12052—
ReactantSodium BicarbonateHCID 516892—
Reactant1-Benzothien-2-yl(5-bromo-2-chlorophenyl)methanolHCID 23103383—
SolventChloroformHCID 6212—
Product2-(5-Bromo-2-chlorobenzyl)-1-benzothiopheneHCID 5817845856.6%

Reaction Steps

Then, Et3SiH (9.2 mL, 0.058 mol) and BF3.Et2O (3.6 mL, 0.029 mol) were added sequentially to a chloroform (110 mL) solution of (1-benzothien-2-yl)(5-bromo-2-chlorophenyl)methanol (10.2 g, 0.0288 mol) at −15° C. The reaction mixture was warmed to room temperature and stirred at the temperature for ten hours. After the reaction mixture was added with a saturated sodium bicarbonate aqueous solution, the organic phase was separated, washed with brine and then 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=60:1) to obtain a colorless oily title compound (5.5 g, 56%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08017792B2
Source datasetuspto-grants-2011_09
ORD IDord-33894529788444bd87a284fc54f9c734
Source noteuspto-grants-2011_09