Sodium Carbonate → HCID 58623482, compound

HRID 750404Notes

Reaction equation

HRID 750404 reaction equation
[CH2:1]([C:4]1[S:8][C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C1C(=O)N([Br:21])C(=O)C1.C(=O)([O-])[O-].[Na+].[Na+]>>[Br:21][C:11]1[S:10][C:9]([C:7]2[S:8][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 67184N-bromobutanimideHCID 23093654HCID 23093654, compound

Product 1

HCID 58623482HCID 58623482, compound

Conditions

Temperature
0 °C

Procedure

Next, 8 g (0.038 mol, 1 eq) of the obtained 5-propyl-2,2′-bithiophene was introduced into a three-necked flask, and this was flushed with Ar. To this, 100 ml of THF was added, stirred and cooled to 0° C. To this, 7.4 g (0.042 mol, 1.1 eq) of NBS was added directly. Then, the temperature was returned to the room temperature, and stirred for 12 hours. To this, 10% sodium carbonate aqueous solution was added, this was extracted with diethyl ether, water washed 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-bromo-5′-propyl-2,2′-bithiophene (3 in the chemical reaction formula) was obtained. Yielding quantity was around 8.8 g, and yielding percentage was around 80%.

Workup

  1. customthis was flushed with Ar
  2. additionTo this, 100 ml of THF was added
  3. customwas returned to the room temperature
  4. stirringstirred for 12 hours
  5. extractionthis was extracted with diethyl ether, water
  6. washwashed until pH is 7
  7. customAfter removing Na2SO4
  8. filtrationby filtration
  9. customthe solvent was removed
  10. customThis was purified by silica gel chromatography, and specified substance of 5-bromo-5′-propyl-2,2′-bithiophene (3 in the chemical reaction formula)
  11. customwas obtained
  12. customYielding quantity
  13. customyielding percentage

Sources & evidence

ORD record
ord-5e442e56db814f08992f856173fe0768
Source dataset
uspto-grants-2008_07
Patent number
US07405003B2

Reaction notes

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