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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2177823Generated: November 1, 2026

Toluene → Methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoate

https://huagongshe.com/reaction/2177823

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
Reactant1,3-CyclohexadieneHCID 11605—
ReactantMethyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoateHCID 67107909—
ProductMethyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoateHCID 67107748—

Reaction Conditions

Temperature125 °C

Reaction Steps

A solution of methyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoate (Intermediate 172, 0.5 g), and cyclohexadiene (0.343 g) in toluene (0.5 ml) was sealed in a vial and heated at 125° C. for 3 days. After cooling, the mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-40% to give methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoate (0.455 g) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09067905B2
Source datasetuspto-grants-2015_06
ORD IDord-c76281dd22574dc2a996cb700fb3bfdc
Source noteuspto-grants-2015_06