Hexane → 5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene

HRID 2078763Notes

Reaction equation

HRID 2078763 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C([Li])CCC.CCCCCC.[CH3:47][Sn:48](Cl)([CH3:50])[CH3:49]>C1COCC1.C(OCC)C.O>[CH3:47][Sn:48]([CH3:50])([CH3:49])[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

8

Reactant 4

HCID 8058HexaneHCID 14016Trimethyltin chlorideHCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 575726935-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiopheneYield 90%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A, 100 mg, 0.172 mmol) in 4.0 mL of THF was added dropwise a solution of n-butyllithium in hexane (0.076 mL, 2.5 M, 0.189 mmol) at −78° C. The solution was stirred at −78° C. for 1 hour and a solution of trimethyltin chloride in THF (0.20 mL, 1.0 M, 0.20 mmol) was added in one portion. The solution was warmed to room temperature and 10.0 mL of water and 10.0 mL of diethylether were added. The organic layer was separated and washed twice with 20 mL of water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to yield 5-trimethylstannyl-4,4′-didodecyl-2,2′-bithiophene (29, 0.103 g, 90% yield) as a yellow oil. 1H NMR (CDCl3): δ 0.84-1.64 (m, 46H), 2.58 (m, 4H), 6.77 (s, 1H), 6.99 (s, 1H), 7.13 (s, 1H).

Workup

  1. temperatureThe solution was warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with 20 mL of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c10945dac674ba5b3b6035f54592d77
Source dataset
uspto-grants-2011_04
Patent number
US07928249B2

Reaction notes

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