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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2298468Generated: October 30, 2026

Water → HCID 22173111, compound

https://huagongshe.com/reaction/2298468

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium CarbonateHCID 10340—
Reactant1-Naphthaleneboronic acidHCID 254532—
Reactant7-Bromo-2-methyl-2,3-dihydro-1H-inden-1-oneHCID 15869783—
CatalystTriphenylphosphineHCID 11776—
Catalystpalladium(II) acetateHCID 167845—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 22173111HCID 2217311193%

Reaction Conditions

Temperature80 °C

Reaction Steps

Using a method similar to Example 15a), 56.3 g (0.25 mol) of 7-bromo-2-methyl-1-indanone (2), 47.3 g (0.275 mol) of 1-naphthylboronic acid and 58 g (0.55 mol) of sodium carbonate were placed in 950 ml of dimethoxyethane and 300 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. 560 mg (2.5 mmol) of palladium acetate and 1.31 g (5 mmol) of triphenylphosphine (TPP) were added and the reaction mixture was stirred for 2 hours at 80° C. After addition of 700 ml of water, the mixture was extracted 5 times with 300 ml each time of diethyl ether, the ether phase was washed twice with 300 ml each time of water and with 300 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 63.3 g of (16) as solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06492539B1
Source datasetuspto-grants-2002_12
ORD IDord-74828087904048c4a815741f2e6b6c2d
Source noteuspto-grants-2002_12