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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2362733Generated: October 31, 2026

Dimethylformamide → 1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}pyrrolidine

https://huagongshe.com/reaction/2362733

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
ReactantPyrrolidineHCID 31268—
Reactant2-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 3734506—
SolventDiethyl EtherHCID 3283—
Product1-{[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}pyrrolidineHCID 18525868—

Reaction Conditions

Temperature80 °C

Reaction Steps

A suspension of 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.18 g, 17.44 mmol), potassium carbonate (2.89 g, 20.93 mmol) and N,N-dimethylformamide (75 mL) was treated with pyrrolidine (1.875 mL, 22.67 mmol), and the reaction was heated to 80° C. for 1 hour. The reaction was cooled to ambient temperature, diluted with ether (115 mL), and filtered. The filtrate was concentrated to dryness to provide the title compound. MS ESI(+) m/z 288.2 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691810B2
Source datasetuspto-grants-2014_04
ORD IDord-3e03511f2b134985b06442c0699b26e6
Source noteuspto-grants-2014_04