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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1503370Generated: October 29, 2026

Sodium hydride → 6-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-one

https://huagongshe.com/reaction/1503370

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant1-Indanone, 6-bromo-HCID 139778—
ReactantAlpha-bromo-2-(2-bromoethyl)tolueneHCID 816791—
SolventTetrahydrofuranHCID 8028—
Product6-Bromo-3',4'-dihydro-1'H-spiro[indene-2,2'-naphthalen]-1(3H)-oneHCID 58197583—

Reaction Steps

A mixture of 6-bromo-indan-1-one (3.57 g, 17 mmol), 1-(2-bromo-ethyl)-2-bromomethyl-benzene (4.7 g, 17 mmol) in THF (50 mL) was added NaH (816 mg, 34 mmol) at room temperature, the mixture was refluxed for 2 hours. The mixture was quenched with water, concentrated, then extracted with DCM, washed with brine, dried over Na2SO4, concentrated to 6-bromo-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalen]-1(3H)-one (1.8 g, 33%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09212153B2
Source datasetuspto-grants-2015_12
ORD IDord-a040739f10434f9eae229cbac2728c2e
Source noteuspto-grants-2015_12