Hydrochloric Acid → 2,2'-Bithiophene, 5-phenyl-

HRID 466914Notes

Reaction equation

HRID 466914 reaction equation
[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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 138512-BromothiopheneHCID 27763132-bromo-5-phenylthiopheneHCID 5462224Magnesium

Product 1

HCID 4547572,2'-Bithiophene, 5-phenyl-Yield 69.4%

Reagents, catalysts & solvents 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickelCatalystHCID 3283Diethyl EtherSolvent3×

Procedure

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.

Workup

  1. customAfter the slightly exothermic reaction
  2. customthe solution thus obtained
  3. customThe crystals which precipitated out
  4. customwere isolated
  5. customdried

Sources & evidence

ORD record
ord-c5032b8eae244781a9d4143b3c8a6f8c
Source dataset
uspto-grants-1992_10
Patent number
US05158598

Reaction notes

Loading…