Methyl iodide → 5-Methoxy-2,3-dihydro-1-benzofuran

HRID 1018726Notes

Reaction equation

HRID 1018726 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][CH2:12]Cl.CI>C1COCC1>[CH3:9][O:8][C:6]1[CH:7]=[CH:2][C:3]2[O:10][CH2:11][CH2:12][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 154539192-Bromo-1-(2-chloroethoxy)-4-methoxybenzene

Product 1

HCID 111162255-Methoxy-2,3-dihydro-1-benzofuranYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-1-(2chloroethoxy)4-methoxybenzene (1.38 g, 5.22 mmol) in THF was added 190 mg (7.82 mmol) of Mg and MeI (3 mL). The mixture was sonicated for 2 h and stirred at room temperature for additional 20 h. The reaction was quenched with 3N HCl (50 mL) and extracted with 1:1 hexane/ethyl acetate (3×50 mL). The combined organic extracts were washed with saturated NaHCO3 brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash chromatography (3:1 hexane/ethyl acetate) of the residue gave 0.66 g (85%) of the title compound as a colorless liquid: 1H NMR (400 MHz. CDCl3) d 6.80 (d, 1H), 6.70 (d. 1H), 6.65 (dd, 1H), 4.53 (t, 2H). 3.75 (s, 3H), 3.18 (t, 3H).

Workup

  1. customThe mixture was sonicated for 2 h
  2. customThe reaction was quenched with 3N HCl (50 mL)
  3. extractionextracted with 1:1 hexane/ethyl acetate (3×50 mL)
  4. washThe combined organic extracts were washed with saturated NaHCO3 brine
  5. dry with materialdried (Na2SO4)
  6. customAfter removing the solvent under reduced pressure, flash chromatography (3:1 hexane/ethyl acetate) of the residue

Sources & evidence

ORD record
ord-6525a50aab904490bb1ac8738a798567
Source dataset
uspto-grants-2002_11
Patent number
US06482956B2

Reaction notes

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