Methyl iodide → 2-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

HRID 1383379Notes

Reaction equation

HRID 1383379 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[O:14][CH2:13][CH2:12][O:11]1.[Li][CH2:16]CCC.CI>C1COCC1>[CH3:16][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]1[O:14][CH2:13][CH2:12][O:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 111845031,3-Dioxolane, 2-(2-bromo-5-methoxyphenyl)-HCID 178418339Butyllithium

Product 1

HCID 221712332-(5-Methoxy-2-methylphenyl)-[1,3]dioxolane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-bromo-5-methoxyphenyl)-1,3-dioxolane (5.44 g; 21 mmol; from step (i) above) in THF (dry, 60 mL) was cooled to −78° C. under a nitrogen atmosphere, and n-BuLi (1.4M; 19.5 mL) was added dropwise via syringe. After addition the solution was stirred at −78° C. for 35 minutes, whereafter MeI (13.41 g; 94.5 mmol) was added. The resultant mixture was slowly stirred to attain room temperature, and then quenched with NH4Cl/aq and extracted with ether. The organic phase was dried (Na2SO4) and concentrated, yielding 4.25 g (quantitative) of the sub-title compound as a brown oil.

Workup

  1. additionAfter addition the solution
  2. additionwas added
  3. customto attain room temperature
  4. customquenched with NH4Cl/aq
  5. extractionextracted with ether
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2e56a74d003c4218936b9ff233121b7f
Source dataset
uspto-grants-2001_07
Patent number
US06255301B1

Reaction notes

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