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
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]3Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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).