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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 336608Generated: October 26, 2026

Sodium hydride → 2-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile

https://huagongshe.com/reaction/336608

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant1-AdamantylthiolHCID 99730—
Reactant2-Bromo-6-fluorobenzonitrileHCID 2783139—
SolventDiethyl EtherHCID 3283—
SolventDimethylacetamideHCID 31374—
Product2-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrileHCID 86681265—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of adamantanethiol (1.01 g) in N,N-dimethylacetamide (20 mL) at room temperature was added NaH (0.24 g, 60% in mineral oil) and the reaction was stirred for 10 minutes. 2-Fluoro-6-bromobenzonitrile (1 g) was added and the mixture was heated to 80° C. for 1 hour. The reaction mixture was cooled and diluted with ether (400 mL), and the mixture was washed three times with 1M NaOH solution and once with brine, then dried over sodium sulfate, filtered and concentrated to yield the crude product which was taken on to the next step without purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08889675B2
Source datasetuspto-grants-2014_11
ORD IDord-50cac4bc689b4df49d250c5e8d9219bc
Source noteuspto-grants-2014_11