Sodium Carbonate → 4-(2,4-Dichlorophenyl)-benzoic acid methyl ester

HRID 227887Notes

Reaction equation

HRID 227887 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][C:17]=2[Cl:19])=[CH:6][CH:5]=1)=[O:11]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 12081Methyl 4-bromobenzoateHCID 2734659(2,4-Dichlorophenyl)boronic acid

Product 1

HCID 102657054-(2,4-Dichlorophenyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

4-Bromo-benzoic acid methyl ester (3 g) was dissolved in a mixture of toluene (20 mL) and ethanol (20 mL). 2,4-Dichloro-phenyl boronic acid (3 g) was added followed by 2 M Na2CO3 (20 mL). The mixture was stirred vigorously under N2 and (PPh3)4Pd (0.5 g) added. The mixture was refluxed with stirring for 3 hours under an atmosphere of N2. The solvent was removed under vacuum, the residue was dissolved in ethyl acetate, and washed with water and saturated NaCl solution. After drying (Na2SO4), the solvent was evaporated and the resultant oil purified by column chromatography to give a fluffy white powder, which was recrystallised from ethanol to give the title compound as long needles. 13C NMR (CDCl3): δ 52.3, 127.3, 129.5, 129.5, 129.6, 129.9, 131.9, 133.1, 134.4, 138.1, 142.8 and 166.8. 1H NMR (CDCl3): δ 3.93 (3H, s), 7.27 (2H, m), 7.47 (2H, d, J=8.5 Hz), 7.49 (1H, s) and 8.09 (2H, d, J=8.2 Hz).

Workup

  1. temperatureThe mixture was refluxed
  2. stirringwith stirring for 3 hours under an atmosphere of N2
  3. customThe solvent was removed under vacuum
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with water and saturated NaCl solution
  6. dry with materialAfter drying (Na2SO4)
  7. customthe solvent was evaporated
  8. customthe resultant oil purified by column chromatography
  9. customto give a fluffy white powder, which
  10. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-bb4a67513bff4593b90272fff6fbca2e
Source dataset
uspto-grants-2009_07
Patent number
US07560597B2

Reaction notes

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