Tetrahydrofuran → IN1414, (4,8-bis(5-(2-hexyldecyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane)

HRID 1024830Notes

Reaction equation

HRID 1024830 reaction equation
[CH2:1]([CH:7]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:8][C:9]1[S:13][C:12]([C:14]2[C:25]3[S:24][CH:23]=[CH:22][C:21]=3[C:20]([C:26]3[S:27][C:28]([CH2:31][CH:32]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:29][CH:30]=3)=[C:19]3[C:15]=2[CH:16]=[CH:17][S:18]3)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1COCC1.C([Li])CCC.[CH3:65][Sn:66](Cl)([CH3:68])[CH3:67]>CCCCCC>[CH2:41]([CH:32]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:31][C:28]1[S:27][C:26]([C:20]2[C:19]3[S:18][C:17]([Sn:66]([CH3:68])([CH3:67])[CH3:65])=[CH:16][C:15]=3[C:14]([C:12]3[S:13][C:9]([CH2:8][CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])=[CH:10][CH:11]=3)=[C:25]3[C:21]=2[CH:22]=[C:23]([Sn:66]([CH3:68])([CH3:67])[CH3:65])[S:24]3)=[CH:30][CH:29]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14016Trimethyltin chlorideHCID 67515109HCID 67515109, compoundHCID 178418339Butyllithium

Product 1

HCID 87426092IN1414, (4,8-bis(5-(2-hexyldecyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-2,6-diyl)bis(trimethylstannane)

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

4,8-Bis-[5-(2-hexyl-decyl)-thiophen-2-yl]-1,5-dithia-s-indacene (2.06 g, 2.56 mmol) was added into a 200-mL flask. The system was vacuumed and backfilled with argon 3 times before 80 mL of anhydrous THF was injected. n-Butyl lithium (2.5 M in hexane, 2.3 mL, 5.6 mmol) was added after the mixture was cooled to −78° C. The mixture was stirred at −78° C. for 30 minutes and then at room temperature for one more hour. The system was cooled down to −78° C. again before trimethyltin chloride (0.5 g, 2.5 mmol) was added in portions. Stirring was continued overnight at room temperature. Hexane (200 mL) was added and the organic layer was washed with 150 mL of water. The aqueous layer was extracted with 100 mL of hexane twice. The combined organic layer was dried over anhydrous Na2SO4. Removal of the solvent under vacuum yielded a yellow liquid (2.2 g, 76.0% yield) as the final product after drying in vacuo overnight. 1H NMR (CDCl3, 500 MHz): δ 7.57 (s, 2H), δ 7.21 (d, 2H, J=3.0 Hz), δ 6.78 (d, 2H, J=3.5 Hz), δ 2.76 (d, 4H, J=6.5 Hz), δ 1.62 (s, 2H), δ 1.26˜1.19 (m, 48H), δ 0.76 (m, 12H), δ 0.29 (m, 18H).

Workup

  1. customat room temperature
  2. additionwas added in portions
  3. stirringStirring
  4. waitwas continued overnight at room temperature
  5. washthe organic layer was washed with 150 mL of water
  6. extractionThe aqueous layer was extracted with 100 mL of hexane twice
  7. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  8. customRemoval of the solvent under vacuum

Sources & evidence

ORD record
ord-df9b9eececd049c39cd6a3891139b564
Source dataset
uspto-grants-2014_05
Patent number
US08723028B2

Reaction notes

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