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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 337649Generated: October 29, 2026

Methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate → Methyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoate

https://huagongshe.com/reaction/337649

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoateHCID 67062162—
Catalyst(1,5-Cyclooctadiene)pyridine(tricyclohexylphosphine)iridium hexafluorophosphateHCID 5702647—
SolventDichloromethaneHCID 6344—
ProductMethyl 3-bromo-5-(3-methoxypropyl)-4-methylbenzoateHCID 66895990—

Reaction Steps

To a dichloromethane (0.2 M) solution of methyl 3-bromo-5-[(1E)-3-methoxy-1-propen-1-yl]-4-methylbenzoate (1 eq.) from the previous step was added Crabtree's catalyst (0.01 eq.). The resulting orange red solution was bubbled with hydrogen for 10 min to activate the catalyst and then stirred at RT under a static balloon atmosphere of hydrogen for 3 h. Finally, removal of the volatiles in vacuo afforded the crude title compound as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889714B2
Source datasetuspto-grants-2014_11
ORD IDord-e8d6ee2315324a5fbde85c8cdfcb8ff8
Source noteuspto-grants-2014_11