Hydrochloric Acid → 4-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-methoxy-benzoic Acid

HRID 1831769Notes

Reaction equation

HRID 1831769 reaction equation
[Br:1][C:2]1[C:10]([OH:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22].[C:23](=O)([O-])[O-].[K+].[K+].CBr.Cl>CN(C=O)C.O>[Br:1][C:2]1[C:10]([O:11][CH3:23])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6323Methyl BromideHCID 11430Potassium CarbonateHCID 220524124-Bromo-3-[2-(2,4-dichlorophenyl)ethoxy]-5-hydroxybenzoic acid

Product 1

HCID 220523294-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-methoxy-benzoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

0.2 g (0.49 mmol) of 4-Bromo-3-[2-(2,4-dichlorophenyl)-ethoxy]-5-hydroxy-benzoic acid was dissolved in 5 ml DMF and 0.272 mg (1.97 mmol) of potassium carbonate was added. The solution was cooled to 0° C. and 0.699 g (4.9 mmol) methyl bromide was added. The solution was stirred for 16 h at RT. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/1). The resulting compound was dissolved in 10 ml dioxan and 1 ml water. 2N aqueous NaOH was added to the solution to give a pH of 13. The reaction solution was heated at 60° C. for 4 h. 5 ml water was added, followed by concentrated hydrochloric acid to give a pH of 1–2, whereupon the product precipitated from solution. The suspension was stirred for 30 min, then the product was filtered off and dried under reduced pressure.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/n-heptane (1/1)
  3. dissolutionThe resulting compound was dissolved in 10 ml dioxan
  4. addition2N aqueous NaOH was added to the solution
  5. customto give a pH of 13
  6. temperatureThe reaction solution was heated at 60° C. for 4 h
  7. customto give a pH of 1–2
  8. customwhereupon the product precipitated from solution
  9. stirringThe suspension was stirred for 30 min
  10. filtrationthe product was filtered off
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-8643b1ccb5d647a48b4a297e8e7931af
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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