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

HRID 1857565Notes

Reaction equation

HRID 1857565 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 stirr at 0° C. for 15 minutes, then to it was added 90% bromomethyl methylether (4.10 g, 29.50 mmol). 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. customwas quenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-5d93105360a14c9b90d83b606f599a1b
Source dataset
uspto-grants-2000_11
Patent number
US06147111

Reaction notes

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