Water → 4,8-Bis(2-ethylhexyl)-2,6-bis-trimethlstannylbenzo[1,2-b:4,5-b']dithiophene

HRID 2195096Notes

Reaction equation

HRID 2195096 reaction equation
[CH2:1]([CH:3]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:4][C:5]1[C:13]2[S:14][CH:15]=[CH:16][C:12]=2[C:11]([CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])=[C:7]2[S:8][CH:9]=[CH:10][C:6]=12)[CH3:2].C([Li])CCC.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36].O>O1CCCC1>[CH2:23]([CH:18]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][C:11]1[C:7]2[S:8][C:9]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:10][C:6]=2[C:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:25][CH2:26][CH2:27][CH3:28])=[C:13]2[S:14][C:15]([Sn:35]([CH3:37])([CH3:36])[CH3:34])=[CH:16][C:12]=12)[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 596092024,8-Bis(2-ethylhexyl)benzo[1,2-b:4,5-b']dithiopheneHCID 178418339Butyllithium

Product 1

HCID 584349014,8-Bis(2-ethylhexyl)-2,6-bis-trimethlstannylbenzo[1,2-b:4,5-b']dithiopheneYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,8-bis(2-ethylhexyl)benzo[1,2-b:4,5-b′]dithiophene (237 mg, 0.57 mmol) in dry tetrahydrofuran (11 mL) was added n-butyllithium (2.5 M in hexane, 0.5 mL, 1.25 mmol) at −78° C. After 1 hour, trimethyltin chloride (264 mg, 1.32 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours, poured into water (20 mL) 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 (437 mg, yield 100%). Upon standing in a freezer for 2 days, pale yellow crystals emerged and were collected (326 mg, yield 77%). 1H NMR (CDCl3, 500 MHz) δ=7.51 (s, 2H), 3.07-3.23 (m, 4H), 1.96-2.07 (m, 2H), 1.21-1.50 (m, 16H), 0.94 (t, J=7.0 Hz, 6H), 0.89 (t, J=7.0 Hz, 6H), 0.46 (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 (437 mg, yield 100%)
  6. waitUpon standing in a freezer for 2 days
  7. customwere collected (326 mg, yield 77%)

Sources & evidence

ORD record
ord-dc713c775ea848c9ae2fb7cec8cdd6d4
Source dataset
uspto-grants-2012_12
Patent number
US08334456B2

Reaction notes

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