Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1600928Generated: October 30, 2026

Toluene → (2R)-1-(3'-Fluorobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

https://huagongshe.com/reaction/1600928

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
Reactant3-Fluorophenylboronic acidHCID 2733986—
Reactant(2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanolHCID 53756856—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
Product(2R)-1-(3'-Fluorobiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanolHCID 53684514—

Reaction Conditions

Temperature110 °C

Reaction Steps

Prepared according to the method described in Example 33a) from toluene (5 ml), ethanol (3 ml), aqueous sodium carbonate (2 M, 1 ml), (2R)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.25 g), ethanol (1 ml), 3-fluorobenzeneboronic acid (0.16 g) and tetrakis(triphenylphosphine)palladium(0) (60 mg) with heating at 110° C. for 4 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate to give the title compound after trituration with diethyl ether:hexane (1:1) as a white solid (0.13 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05977105
Source datasetuspto-grants-1999_11
ORD IDord-d4f1860d1a0d443a9e1481766ec451a4
Source noteuspto-grants-1999_11