Water → HCID 58991608, compound

HRID 1504245Notes

Reaction equation

HRID 1504245 reaction equation
[CH2:1]([CH:3]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:4][Si:5]1([CH2:24][CH:25]([CH2:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH3:29])[C:9]2[CH:10]=[C:11]([Si](C)(C)C)[S:12][C:8]=2[C:7]2[S:17][C:18]([Si](C)(C)C)=[CH:19][C:6]1=2)[CH3:2].FC(F)(F)C(O)=O.O>C(Cl)(Cl)Cl>[CH2:30]([CH:25]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:24][Si:5]1([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:32][CH2:33][CH2:34][CH3:35])[C:9]2[CH:10]=[CH:11][S:12][C:8]=2[C:7]2[S:17][CH:18]=[CH:19][C:6]1=2)[CH3:31]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 582891994,4-Bis(2-ethylhexyl)-2,6-bis(trimethylsilyl)-4H-silolo[3,2-b:4,5-b′]dithiophene

Product 1

HCID 58991608HCID 58991608, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4,4-bis(2-ethylhexyl)-2,6-bis(trimethylsilyl)-dithieno[3,2-b:2′,3′-d]silole (Compound G1, synthesized in accordance with Non-patent Document J. Am. Chem. Soc. 2008, 130, 16144-16145, 1.03 g, 1.786 mmol) was placed in a 200 mL four-necked recovery flask in a nitrogen atmosphere, and dissolved in chloroform (50 mL). Trifluoroacetic acid (0.265 mL, 3.573 mmol) was added dropwise, and the mixture was agitated for about 3.5 hours. Water was added to the reaction solution, and the lower layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure. This was dissolved in hexane and subjected to silica gel column chromatography (solvent: hexane) to obtain 4,4-bis(2-ethylhexyl)-dithieno[3,2-b:2′,3′-d]silole (Compound G2) as a light yellow oily substance (702 mg, yield 94%).

Workup

  1. washthe lower layer was washed with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThis was dissolved in hexane

Sources & evidence

ORD record
ord-9ed3cdddb39a4cc9bd7a03d4a71545b6
Source dataset
uspto-grants-2015_12
Patent number
US09212254B2

Reaction notes

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