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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2121767Generated: November 2, 2026

3-Bromo-5-fluorobenzonitrile → 6-(3-Cyano-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline

https://huagongshe.com/reaction/2121767

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Bromo-5-fluorobenzonitrileHCID 2783330—
Reactant(1-(tert-Butoxycarbonyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)boronic acidHCID 10615401—
Product6-(3-Cyano-5-fluorophenyl)-1,2-dihydro-2,2,4-trimethylquinolineHCID 983901338.6%

Reaction Steps

This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (46.3 mg, 0.14 mmol) and 3-bromo-5-fluorobenzonitrile (29.1 mg, 0.14 mmol). The crude material was purified by recrystallization from hexane to afford 15.8 mg (37%) of Compound 271. Data for Compound 271: 1H NMR (400 MHz, acetone-d6) 7.83 (app t, J=1.3, 1H), 7.68 (dd, J=10.6, 4.0, 1H), 7.43 (d, J=2.0, 1H), 7.41 (dd, J=2.2, 1.2 1H) 7.35 (dd, J=8.3, 2.2, 1H), 6.59 (d, J=8.4, 1H), 5.35 (br s, 1H), 5.39 (s, 1H), 2.04 (s, 3H), 1.28 (s, 6H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06696459B1
Source datasetuspto-grants-2004_02
ORD IDord-c922ba939c1d47f88c32484a19d7ff90
Source noteuspto-grants-2004_02