Citric Acid → 3-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

HRID 1670719Notes

Reaction equation

HRID 1670719 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Br:19][C:20]1[C:21]([OH:31])=[C:22]([O:28][CH2:29][CH3:30])[CH:23]=[C:24]([CH:27]=1)[CH:25]=[O:26].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:31][C:21]2[C:22]([O:28][CH2:29][CH3:30])=[CH:23][C:24]([CH:25]=[O:26])=[CH:27][C:20]=2[Br:19])[CH:5]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 6124963-Bromo-5-ethoxy-4-hydroxybenzaldehyde

Product 1

HCID 866244083-(2-Bromo-6-ethoxy-4-formylphenoxymethyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

3-Bromomethylbenzoic acid methyl ester (0.77 g), K2CO3 (1.0 g) and a catalytic amount of n-Bu4NI were added to a solution of 5-bromo-3-ethoxy-4-hydroxybenzaldehyde (0.75 g) in 10 mL DMF and the reaction mixture was stirred at 70° C. for 1 h. A solution of 3% citric acid in water was added and the reaction mixture was extracted with ethyl acetate. The organic phases were washed with water and brine, dried over MgSO4 and concentrated. The title compound was obtained after flash column chromatography (silica gel, heptane/ethyl acetate (1/4, v/v), Rf=0.25).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic phases were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5ad6e7ba929e47ae901675011fb6676b
Source dataset
uspto-grants-2011_08
Patent number
US07994189B2

Reaction notes

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