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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 82048Generated: October 26, 2026

Methylamine → 6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-one

https://huagongshe.com/reaction/82048

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
ReactantMethyl 5-bromo-2-(bromomethyl)benzoateHCID 12929136—
SolventTetrahydrofuranHCID 8028—
Product6-bromo-2-methyl-2,3-dihydro-1H-isoindol-1-oneHCID 46942008100%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 5-bromo-2-bromomethyl-benzoic acid methyl ester (1.00 g, 3.25 mmol) in THF (6.5 mL) was a solution of methylamine in THF (2M, 8.12 mL, 16.24 mmol). The reaction mixture was heated at 50° C. for 4 hours and then concentrated under vacuum. The residue was taken up in EtOAc and the organic layer was then washed with an aqueous 1M HCl solution, brine, dried (Na2SO4), filtered, concentrated under vacuum to give the title compound (0.73 g, 100%) as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08846712B2
Source datasetuspto-grants-2014_09
ORD IDord-6e174c0561454a2d8fc1dd1e6727ca38
Source noteuspto-grants-2014_09