Methyl iodide → 2-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene

HRID 1798079Notes

Reaction equation

HRID 1798079 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:4][C:3]=1[CH2:16][OH:17].[H-].[Na+].[CH3:20]I>C1COCC1>[Br:1][C:2]1[C:3]([CH2:16][O:17][CH3:20])=[CH:4][C:5]([O:12][CH2:13][O:14][CH3:15])=[CH:6][C:7]=1[O:8][CH2:9][O:10][CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10957768[2-Bromo-3,5-bis(methoxymethoxy)phenyl]methanol

Product 1

HCID 582927852-Bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2-bromo-3,5-bis-methoxymethoxy-phenyl)-methanol (10.2 g, 33.3 mmol) in THF (60 mL) was treated with NaH (2.67 g, 66.7 mmol) at 0° C. The resulting suspension was stirred at room temperature for 20 min. CH3I was added to the mixture and the reaction was stirred at room temperature for 1 h. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=5:1) to afford the title compound (10.5 g, 96%). 1H NMR (300 MHz, CDCl3) δ 6.88 (s, 1H), 6.80 (s, 1H), 5.23 (s, 2H), 5.17 (s, 2H), 4.50 (s, 2H), 3.51 (s, 3H), 3.47 (s, 6H).

Workup

  1. stirringthe reaction was stirred at room temperature for 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica, hexanes/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a8d8b337929e4daabfae278476c72868
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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