Water → HCID 58453910, compound

HRID 2078758Notes

Reaction equation

HRID 2078758 reaction equation
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].O>C1COCC1>[CH2:29]([Sn:24]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:25][CH2:26][CH2:27][CH3:28])[C:3]1[S:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 962WaterHCID 15096Tributyltin ChlorideHCID 5462224MagnesiumHCID 104268162-Bromo-3-Dodecylthiophene

Product 1

HCID 58453910HCID 58453910, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To magnesium turnings (0.160 g, 6.6 mmol) in anhydrous THF (8.0 mL), heated to maintain a mild reflux, was added dropwise 2-bromo-3-dodecylthiophene (23; 2.00 g, 6.0 mmol). The reaction mixture was refluxed for 2 hours before being transferred to a solution of tributyltin chloride (1.80 mL, 6.41 mmol) in 10.0 mL of anhydrous THF at −78° C. The mixture was warmed to room temperature and stirred overnight before being poured into water. The aqueous layer was extracted with hexanes and the combined organic phase was washed with brine and dried over magnesium sulfate. After filtration, the solvent was removed in vacuo to yield 2-tributylstannyl-3-dodecylthiophene (24) as a yellow liquid (3.10 g, 95% yield). 1H NMR (CDCl3): δ 0.90-1.63 (m, 50H), 2.62 (t, 2H), 7.12 (d, 1H, J=4.5 Hz), 7.55 (d, 1H, J=4.5 Hz) ppm.

Workup

  1. temperatureto maintain a mild reflux
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. extractionThe aqueous layer was extracted with hexanes
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2d913c913a224ed7bb97e10e6e63b3fb
Source dataset
uspto-grants-2011_04
Patent number
US07928249B2

Reaction notes

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