Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylate → Didodecyl benzo[1,2-b:4,5-b']dithiophene-4,8-dicarboxylate

HRID 335355Notes

Reaction equation

HRID 335355 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](C(OCCCCCCCCCCCC)=O)([C:43]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[O:44])[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](C(OCCCCCCCCCCCC)=O)([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])[C:2]1=2>CN(C=O)C>[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([C:43]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[O:44])=[C:7]3[C:11](=[C:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])[C:2]1=2)[CH:10]=[CH:9][S:8]3

Participants

3

Reactant 1

HCID 86711081Tetradodecyl benzo[1,2-b:4,5-b']dithiophene-4,4,8,8-tetracarboxylate

Product 1

HCID 70983717Didodecyl benzo[1,2-b:4,5-b']dithiophene-4,8-dicarboxylateYield 32.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

In a one-necked flask, tetradodecyl benzo[1,2-b:4,5-b′]dithiophene-4,4,8,8-tetracarboxylate (9.0 g, 8.65 mmol) was dispersed in DMF (80 mL). The mixture was stirred at 120° C. for 10 minutes until the solution became clear. After air was purged in the flask, NaI (800 mg) was added and the reaction mixture was refluxed for 24 hours. After the solvent was evaporated under vacuum, water (30 mL) was added to the residue to form a mixture, which was extracted with CH2Cl2. The organic layer was combined, dried, and concentrated. The crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=7:3) to give didodecyl benzo[1,2-b:4,5-b′]dithiophene-4,8-dicarboxylate (yield: 1.75 g, 32.9%). 1H NMR (CDCl3): 0.9 (6H, t), 1.3 (28H, m), 1.4 (4H, m), 1.6 (4H, m), 1.9 (4H, m), 4.6 (4H, t), 7.8 (2H, d), 8.3 (2H, d).

Workup

  1. customAfter air was purged in the flask, NaI (800 mg)
  2. additionwas added
  3. temperaturethe reaction mixture was refluxed for 24 hours
  4. customAfter the solvent was evaporated under vacuum, water (30 mL)
  5. additionwas added to the residue
  6. customto form a mixture, which
  7. extractionwas extracted with CH2Cl2
  8. customdried
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography (eluent: CH2Cl2:hexane=7:3)

Sources & evidence

ORD record
ord-d3afdc33ba9d4c98981212f2b6a3c6d2
Source dataset
uspto-grants-2014_11
Patent number
US08883954B2

Reaction notes

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