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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1485996Generated: October 27, 2026

Tetrabutylammonium Fluoride → 2-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid

https://huagongshe.com/reaction/1485996

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant2-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid 2-trimethylsilanyl-ethyl esterHCID 68603265—
SolventTetrahydrofuranHCID 8028—
Product2-(3-Tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acidHCID 6860280275%

Reaction Steps

A mixture of 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid 2-trimethylsilanyl-ethyl ester (1.3 g, 2.2 mmol) and tetrabutyl-ammonium fluoride (6.6 mL, 6.6 mmol, 1 M in THF) in THF (20 mL) was stirred at rt for 30 minutes. The mixture was then concentrated and diluted with ether. The ether layer was washed with water, dried and concentrated to yield 2-(3-tert-butoxycarbonyl-propoxy)-4-chloro-5-(4-cyano-6-trifluoromethyl-pyridin-3-yl)-benzoic acid (0.8 g). MS [M+H]+: 485.1; tR=2.96 min (method 1)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09422310B2
Source datasetuspto-grants-2016_08
ORD IDord-fb76378b3605483d80d1372e115a0add
Source noteuspto-grants-2016_08