[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.Br[C:9]1[S:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.Cl>CCOCC.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:14]1([C:12]2[S:13][C:9]([C:3]3[S:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
In 140 ml of ether, 17.4 g (0.725 mol) of magnesium shavings was reacted according to Grignard with 118 g (0.723 mol) of 2-bromothiophene, and this solution was then introduced into 280 ml of ether, 1.5 g (2.8 mmol) of 1,3-bis(diphenylphosphino)propane nickel dichloride and 140 g (0.586 mol) of 5-bromo-2-phenylthiophene. After the slightly exothermic reaction had subsided, the mixture was stirred for 4 hours at boiling point, and the solution thus obtained was then diluted with 280 ml of ether and stirred into 280 ml of 2N hydrochloric acid solution. The crystals which precipitated out were isolated and dried. There was obtained 98.4 g (69.4% of theory) of 5-phenyl-[2,2'-bithienyl], mp. 116.5°-118° C.
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