Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | 7-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one | HCID 11789822 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethylene Glycol | HCID 174 | — |
| Product | HCID 22173443 | HCID 22173443 | 93.9% |
Reaction Steps
Using a method similar to Example 16d), 6.28 g (0.035 mol) of (1), 7.6 g (0.040 mol) of 4-trifluoromethylphenylboronic acid and 8.16 g (77.3 mmol) of sodium carbonate were placed in 160 ml of ethylene glycol/17 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 57 mg (0.283 mmol) of palladium acetate and 0.47 g (0.848 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 170 ml of water, the aqueous phase was extracted 4 times with 100 ml each time of ether, the combined ether phases were washed with 60 ml of water and 60 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 9.54 g of 2-methyl-7-(4-trifluoromethylphenyl)-1-indanone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06492539B1 |
|---|
| Source dataset | uspto-grants-2002_12 |
|---|
| ORD ID | ord-3902d7e92add44919f1160e37f833e88 |
|---|
| Source note | uspto-grants-2002_12 |
|---|