Water → HCID 58991608, compound

HRID 1772575Notes

Reaction equation

HRID 1772575 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-b6cf251883d1461f82000f2d5913edda
Source dataset
uspto-grants-2016_02
Patent number
US09249257B2

Reaction notes

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