Potassium Carbonate → 3-Bromo-5-ethoxy-4-[(3-nitrobenzyl)oxy]benzaldehyde

HRID 910743Notes

Reaction equation

HRID 910743 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:22][CH2:23][CH3:24])[C:20]=1[OH:21])[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:22][CH2:23][CH3:24])[C:20]=1[O:21][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH:16]=[O:17]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 5858403-Bromo-5-ethoxy-4-[(3-nitrobenzyl)oxy]benzaldehyde

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-nitrobenzylbromide (2 g), 3-bromo-5-ethoxy-4-hydroxy benzaldehyde (2.06 g), K2CO3 (2.55 g) and Bu4NI (186 mg) in DMF (50 ml) was stirred at 60° C. for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystallized from heptane.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-cfb5c841b89a46d88744f1c574ef5d07
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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