10 g (37.7 mmol) of 4-Bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1b), 5.5 g (45.3 mmol) of phenylboronic acid, 8.8 g (80 mmol) of sodium carbonate, 80 ml of ethylene glycol and 12 ml of water were placed under a protective argon atmosphere and heated to 80° C. While stirring vigorously freshly prepared catalyst solution of 20 mg of palladium (II) acetate, 260 mg of 3,3′,3″-phoshinidynetris(benzenesulfonic acid)trisodium salt (TPPTS) in 4 ml of water were added to the reaction and the reaction mixture was refluxed for 3 hrs. After cooling to room temperature, 40 ml of water was added and the ethylene glycol phase was extracted three times with a total of 240 ml of toluene. The combined organic phases were washed twice with a total of 250 ml of aqueous sodium chloride and dried over 150 g of sodium sulfate. Removal of solvents gave 9.6 g of brawn oil, which was gradually crystallized (97%, GC-MS).
