Dimethylformamide → ST51040321

HRID 1167634Notes

Reaction equation

HRID 1167634 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].Br[CH2:14][O:15][CH3:16].CN([CH:20]=[O:21])C>>[CH3:14][O:15][CH2:16][O:1][C:2]1[CH:7]=[C:6]([O:21][CH3:20])[CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 69472-NitrophenolHCID 24758Sodium hydrideHCID 83093Bromomethyl methyl ether

Product 1

HCID 12210185ST51040321Yield 88%

Conditions

Temperature
0 °C

Procedure

To a solution of hydroxynitrobenzene (21.2 g, 0.125 mol) in DMF (250 ml) was added sodium hydride (4.5 g, 0.188 mol) at 0° C. under argon. The mixture was allowed to stir at 0° C. for 1 h, then bromomethyl methylether (22 ml, 0.150 mol) was added. After stirring for 18 h at rt the reaction was quenched with water. The mixture was extracted with ethyl acetate (3×30 ml) and the combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduce pressure gave the title compound as a brown oil (23.4 g, 88%).

Workup

  1. stirringAfter stirring for 18 h at rt the reaction
  2. customwas quenched with water
  3. extractionThe mixture was extracted with ethyl acetate (3×30 ml)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-e130adefaa7b476db8a01eac5761c489
Source dataset
uspto-grants-2003_09
Patent number
US06620826B2

Reaction notes

Loading…