Methylparaben → HCID 59428082, compound

HRID 1095096Notes

Reaction equation

HRID 1095096 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[OH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([O:17][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=[O:8])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 59428082HCID 59428082, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (4.04 g, 20 mmol) (Alfa) in N,N-dimethylacetamide (30 mL) was added anhydrous K2CO3 (2.76 g, 20 mmol), and methyl 4-hydroxybenzoate (3.1 g, 20 mmol, Aldrich). The reaction mixture was heated at 170° C. for 1 h. The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, brine. The organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc: hexanes=1:8 then 1:4) to give 4-(4-bromo-2-formyl-phenoxy)-benzoic acid methyl ester as a white solid (Yield 6.4 g, 95%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with water, brine
  3. customThe organic layer was separated
  4. extractionaqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (EtOAc

Sources & evidence

ORD record
ord-e099bf2b48d145589accdd35cee5a124
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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