Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Naphthaleneboronic acid | HCID 254532 | — |
| Reactant | 7-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one | HCID 15869783 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 22173111 | HCID 22173111 | 93% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06492539B1 |
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| Source dataset | uspto-grants-2002_12 |
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| ORD ID | ord-74828087904048c4a815741f2e6b6c2d |
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| Source note | uspto-grants-2002_12 |
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