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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2175299Generated: October 29, 2026

2,4,5-Trichlorophenol → (5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-((3-chloro-2-methylphenoxy)methyl)cyclopropyl)methanone

https://huagongshe.com/reaction/2175299

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2,4,5-TrichlorophenolHCID 7271—
Reactant3-Chloro-o-cresolHCID 14856—
ReactantEthyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetateHCID 70982627—
ReactantEthyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetateHCID 70983434—
Reactant(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-(hydroxymethyl)cyclopropyl)methanoneHCID 86712601—
Product(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-((3-chloro-2-methylphenoxy)methyl)cyclopropyl)methanoneHCID 86712602—

Reaction Steps

The title compound was prepared using a procedure analogous to ethyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate except that ethyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate was replaced with (5-bromo-3,4-dihydroquinolin-1(2H)-yl)(1-(hydroxymethyl)cyclopropyl)methanone and 2,4,5-trichlorophenol was replaced with 3-chloro-2-methylphenol. LCMS, [M+H]+=436.1. 1H NMR (400 MHz, CDCl3) δ 7.54 (d, J=8.2 Hz, 1H), 7.33 (d, J=7.9 Hz, 1H), 7.04-6.90 (m, 3H), 6.49 (d, J=7.8 Hz, 1H), 3.92-3.82 (m, 4H), 2.65 (t, J=6.9 Hz, 2H), 2.26 (s, 3H), 1.96-1.87 (m, 2H), 1.21 (dd, J=6.9, 4.9 Hz, 2H), 0.94 (q, J=5.0 Hz, 2H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09062028B2
Source datasetuspto-grants-2015_06
ORD IDord-53b644ac9de843bbadf8506adb7ccf13
Source noteuspto-grants-2015_06