Hydrochloric Acid → HCID 59753246, compound

HRID 750405Notes

Reaction equation

HRID 750405 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][C:9]([CH2:12][CH2:13][CH3:14])=[CH:10][CH:11]=2)=[CH:4][CH:3]=1.Br[C:16]1[S:17][CH:18]=CC=1.Cl.C(O[CH2:25][CH3:26])C>[Ni]>[CH2:12]([C:9]1[S:8][C:7]([C:5]2[S:6][C:2]([C:16]3[S:17][CH:18]=[CH:25][CH:26]=3)=[CH:3][CH:4]=2)=[CH:11][CH:10]=1)[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 138512-BromothiopheneHCID 58623482HCID 58623482, compound

Product 1

HCID 59753246HCID 59753246, compound

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
0 °C

Procedure

Next, 8 g (0.028 mol, 1 eq) of the obtained 5-bromo-5′-propyl-2,2′-bithiophene and 0.04 g (0.07 mmol, 0.0025 eq) of Ni (dppp) Cl2 were introduced into a three-necked flask, and this was flushed with Ar. To this, 100 ml of diethyl ether was added and stirred (reaction fluid α). 0.94 g (0.0385 mol, 1.38 eq) of Mg was introduced to another three-necked flask, and flushed with Ar. To this, 50 ml of diethyl ether was added and stirred. To this, a solution, of which 5.7 g (0.035 mol, 1.25 eq) of 2-bromothiophene was diluted with 50 ml of diethyl ether, was dropped. After dropping, this was refluxed for 2 hours, and was laid for cooling (reaction fluid β). The reaction fluid β was dropped to the reaction fluid α, which was cooled to 0° C. After dropping, this was stirred for 2 hours and was refluxed for 12 hours. This was cooled to 0° C., 30 ml of 2N—HCl was dropped. After dropping, the temperature was returned to the room temperature, and stirred for 2 hours. This was extracted with chloroform, water washed with Na2CO3 aqueous solution until pH is 7, and dehydrated with Na2SO4. After removing Na2SO4 by filtration, the solvent was removed. This was purified by silica gel chromatography, and specified substance of 5-propyl-2,2′:5′,2″-terthiophene (4 in the chemical reaction formula) was obtained. Yielding quantity was around 6 g, and yielding percentage was 75%.

Workup

  1. customthis was flushed with Ar
  2. additionTo this, 100 ml of diethyl ether was added
  3. custom(reaction fluid α)
  4. customflushed with Ar
  5. additionTo this, 50 ml of diethyl ether was added
  6. stirringstirred
  7. additionwas dropped
  8. temperaturethis was refluxed for 2 hours
  9. temperaturefor cooling
  10. custom(reaction fluid β)
  11. additionThe reaction fluid β was dropped to the reaction fluid α, which
  12. stirringthis was stirred for 2 hours
  13. temperaturewas refluxed for 12 hours
  14. temperatureThis was cooled to 0° C.
  15. customwas returned to the room temperature
  16. stirringstirred for 2 hours
  17. extractionThis was extracted with chloroform, water
  18. washwashed with Na2CO3 aqueous solution until pH is 7
  19. customAfter removing Na2SO4
  20. filtrationby filtration
  21. customthe solvent was removed
  22. customThis was purified by silica gel chromatography, and specified substance of 5-propyl-2,2′:5′,2″-terthiophene (4 in the chemical reaction formula)
  23. customwas obtained
  24. customYielding quantity
  25. customyielding percentage

Sources & evidence

ORD record
ord-7ebc3a09be5b4f3bba59f27072dae409
Source dataset
uspto-grants-2008_07
Patent number
US07405003B2

Reaction notes

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