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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1410118Generated: October 24, 2026

Triethylamine → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

https://huagongshe.com/en/reaction/1410118

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 2734621—
SolventDichloromethaneHCID 6344—
Product4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 276058848.8%

Reaction Steps

To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45%) as a yellow solid. LC-MS: 248 [M+H]+, tR=1.421 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08921383B2
Source datasetuspto-grants-2014_12
ORD IDord-55d2ce2fcf2240fba99cca6a54a2cb97
Source noteuspto-grants-2014_12