Sodium hydride → 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene

HRID 1586030Notes

Reaction equation

HRID 1586030 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].Br[CH2:14][O:15][CH3:16]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH2:14][O:15][CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 83093Bromomethyl methyl etherHCID 134938392-Bromo-5-methoxyphenol

Product 1

HCID 148270371-Bromo-4-methoxy-2-(methoxymethoxy)benzeneYield 106.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-Bromo-2-hydroxy-4-methoxybenzene (5.00 g, 24.60 mmol) in DMF was added 60% sodium hydride (1.97 g, 49.20 mmol) at 0° C. under argon. The mixture was allowed to stir at 0° C. for 15 minutes, then 90% bromomethyl methylether (4.10 g, 29.50 mmol) was added. After stirring for 1 h at 0° C. the reaction was quenched with water. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent afforded the title compound as an oil (6.5 g, quantitative yield). 1H NMR (400 MHz, CDCl3) δ 7.41 (d, 2H), 6.76 (d, 1H), 6.47 (dd, 1H), 5.24 (s, 2H), 3.87 (s, 3H), 3.53 (s, 3H).

Workup

  1. stirringAfter stirring for 1 h at 0° C. the reaction
  2. customwas quenched with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-6268778ccd884063b5c06ad2c0596dd2
Source dataset
uspto-grants-1999_08
Patent number
US05942516

Reaction notes

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