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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1921844Generated: October 30, 2026

Thionyl Chloride → 2-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-one

https://huagongshe.com/reaction/1921844

Reaction equation

Participants

RoleNameHCIDCharge
ReactantThionyl ChlorideHCID 24386—
Reactant5-Bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acidHCID 59023023—
SolventDichloromethaneHCID 6344—
Product2-Bromo-5-(4-methoxy-benzyl)-3a,5,6,6a-tetrahydro-furo[2,3-c]pyrrol-4-oneHCID 5902303728.6%

Reaction Steps

A solution of 5-bromo-2-[(4-methoxy-benzylamino)-methyl]-furan-3-carboxylic acid (618 mg, 1.82 mmol) and SOCl2 (0.136 mL) in DCM (2 mL) is stirred at 85° C. for 18 hours. The mixture is concentrated in vacuo and purified by silica gel column chromatography eluting with 7:3 petroleum ether:ethyl acetate to afford the title compound (0.169 g, 28%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08173656B2
Source datasetuspto-grants-2012_05
ORD IDord-0f57974bffc446e495cf59f332fee80f
Source noteuspto-grants-2012_05