Methyl iodide → HCID 89480002, compound

HRID 589236Notes

Reaction equation

HRID 589236 reaction equation
[Li][CH2:2]CCC.[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH:17]=2)[S:10][C:11]=1Br.IC>C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([C:13]2[S:14][C:15]([CH3:19])=[C:16]([CH3:18])[CH:17]=2)[S:10][C:11]=1[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 89479747HCID 89479747, compoundHCID 178418339Butyllithium

Product 1

HCID 89480002HCID 89480002, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (2.5M in hexane) (10 mL, 25 mmol) was added dropwise to a solution of 4,5-dibromo-4′,5′-dimethyl-2,2′-bithiophene (3.37 g, 9.57 mmol) in 100 mL of THF at −78° C. After 90 minutes upon addition, excess iodomethane (3.6 g, 25 mmol) was added dropwise by syringe, and the mixture was stirred for 30 min, then warmed to RT and stirred for another 3 hours. Solvents were evaporated and the residue was poured into water. The mixture was extracted with hexanes, dried over MgSO4, and the solvent was evaporated to give off-yellow solid (2.71 g, 9.43 mmol, 99% yield) of 4-bromo-4′,5,5′-trimethyl-2,2′-bithiophene. 1H NMR (600 MHz, CDCl3) δ 6.85 (s, 1H), 6.82-6.76 (m, 1H), 2.37 (s, 3H), 2.33 (s, 3H), 2.11 (s, 3H)

Workup

  1. additionwas added dropwise by syringe
  2. stirringstirred for another 3 hours
  3. customSolvents were evaporated
  4. additionthe residue was poured into water
  5. extractionThe mixture was extracted with hexanes
  6. dry with materialdried over MgSO4
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6018663e0afd441d8cc0b9be5bb361c9
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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