Hydrochloric Acid → 3,3'-Dihexyl-2,2'-bithiophene

HRID 278832Notes

Reaction equation

HRID 278832 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]1[S:16][CH:17]=[CH:18][C:19]=1Br.Cl>C(OCC)C.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:10]1[CH:14]=[CH:13][S:12][C:11]=1[C:15]1[S:16][CH:17]=[CH:18][C:19]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8190873,3'-Dibromo-2,2'-bithiopheneHCID 178444609HCID 178444609, compound

Product 1

HCID 114844383,3'-Dihexyl-2,2'-bithiopheneYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

Hexylmagnesium bromide (100 ml, 2 M solution in diethyl ether, 200 mol) was added dropwise to a solution of 3,3′-dibromo-2,2′-bithiophene (15 g, 46.6 mmol) and Ni(dppp)Cl2 (0.5 g, 0.1 mmol) in 100 ml of diethyl ether at 0° C. The reaction was slightly exothermic and a red brown coloration was observed. After stirred and heated for 24 h, the reaction mixture was cautiously poured into a mixture of crushed ice and diluted HCl solution and extracted with ether. The combined extracts were dried over anhydrous MgSO4 and filtered. After removal of the solvent, the residue was vacuum-distilled to give a clear viscous oil (15.6 g, 81%). 1H-NMR (CDCl3, ppm): δ7.25 (d, 2H, J=5 Hz), 6.96 (d, 2H, J=5 Hz), 2.50 (t, 4H), 1.54 (m, 4H), 1.23 (m, 12H), 0.85 (t, 6H).

Workup

  1. temperatureheated for 24 h
  2. extractionextracted with ether
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customAfter removal of the solvent
  6. distillationthe residue was vacuum-distilled

Sources & evidence

ORD record
ord-843b4f64706a48bc96d032b421ba5e52
Source dataset
uspto-grants-2002_03
Patent number
US06361717B1

Reaction notes

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