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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 878703Generated: November 4, 2026

Toluene → HCID 68699250, compound

https://huagongshe.com/reaction/878703

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium Phosphate, TribasicHCID 62657—
ReactantCyclopropylboronic acidHCID 2760897—
ReactantMethyl 4-Bromo-2-chlorobenzoateHCID 22058730—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
ProductHCID 68699250HCID 6869925063.2%

Reaction Conditions

Temperature110 °C

Reaction Steps

Charged methyl 4-bromo-2-chlorobenzoate (1.50 g, 6.01 mmol), cyclopropylboronic acid (931 mg, 10.82 mmol), Pd(PPh3)4 (347 mg, 0.30 mmol), K3PO4 (1.82 g, 18.04 mmol), toluene (15 mL) and water (15 mL) to a flask, the mixture was then purged with nitrogen, and heated to 110° C. overnight. It was then cooled to room temperature and filtered, the filtrate was extracted with ethylacetate twice, concentrated the organic phase and purified by flash column chromatograph to give 800 mg of the title compound (63%). 1H NMR (400 MHz, CDCl3): δ 0.73-0.77 (2H, m), 0.98-1.07 (2H, m), 1.85-1.90 (1H, m), 3.90 (3H, s), 6.96 (1H, dd, J=1.6 Hz, 8.0 Hz), 7.11 (1H, d, J=1.6 Hz), 7.74 (1H, d, J=8.0 Hz).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08987461B2
Source datasetuspto-grants-2015_03
ORD IDord-0dcb13d2d8e94653984ec476abed8eba
Source noteuspto-grants-2015_03