Water → 4,8-Dioctyl-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiophene

HRID 405042

Reaction equation

HRID 405042 reaction equation
[CH2:1]([C:9]1[C:17]2[S:18][CH:19]=[CH:20][C:16]=2[C:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:11]2[S:12][CH:13]=[CH:14][C:10]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36].O>O1CCCC1>[CH2:1]([C:9]1[C:17]2[S:18][C:19]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:20][C:16]=2[C:15]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[C:11]2[S:12][C:13]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:14][C:10]=12)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 582808924,8-Dioctylbenzo[1,2-b:4,5-b']dithiopheneHCID 178418339Butyllithium

Product 1

HCID 596091954,8-Dioctyl-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiopheneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,8-dioctylbenzo[1,2-b:4,5-b′]dithiophene (782 mg, 1.89 mmol) in dry tetrahydrofuran (36 mL) was added n-butyllithium (2.5 M in hexane, 1.66 mL, 4.15 mmol) at −78° C. After 1 hour, trimethyltin chloride (877 mg, 4.40 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, poured into water and extracted with ether three times. The organic layer was washed with brine and dried over anhydrous MgSO4. Upon evaporating the solvent, a pale yellow oil was obtained (1.03 g, yield 74%). Upon standing for one week, yellow crystals emerged and were collected (413 mg, yield 29%). 1H NMR (CDCl3, 500 MHz) δ=7.51 (s, 2H), 3.22 (t, J=8.0 Hz, 4H), 1.76-1.89 (m, 4H), 1.45-1.54 (m, 4H), 1.22-1.45 (bs, 16H), 0.90 (t, J=7.0 Hz, 6H), 0.47 (s, 18H).

Workup

  1. extractionextracted with ether three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customUpon evaporating the solvent
  5. customa pale yellow oil was obtained (1.03 g, yield 74%)
  6. waitUpon standing for one week
  7. customwere collected (413 mg, yield 29%)

Sources & evidence

ORD record
ord-7a328ffc29174f4f9b05fa4d07f41849
Source dataset
uspto-grants-2014_06
Patent number
US08748739B2

Linked notes

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