4-Fluorophenylboronic acid → Methyl 4-methoxy-2-(4-fluorophenyl)benzoate

HRID 1836423Notes

Reaction equation

HRID 1836423 reaction equation
C(=O)([O-])O.[Na+].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10](S(C(F)(F)F)(=O)=O)[CH:9]=1.[F:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[CH:27][CH:28]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 23499549Methyl 4-methoxy-2-trifluoromethanesulphonylbenzoate

Product 1

HCID 23499548Methyl 4-methoxy-2-(4-fluorophenyl)benzoateYield 131%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Saturated aqueous sodium hydrogen carbonate solution (50 ml) was added to a solution of methyl 4-methoxy-2-trifluoromethanesulphonylbenzoate (6.3 g.) and 4-fluorobenzeneboronic acid (3.36 g.) in DME (150 ml) at ambient temperature under an argon atmosphere. Tetrakis(triphenylphosphine) palladium (928 mg.) was added and the reaction heated and stirred at reflux for 3.5 hours resulting in a homogeneous solution. After cooling to ambient temperature, the reaction was partitioned between ethyl acetate and water. The organic phase was washed with 2N hydrochloric acid, water and brine, filtered through 1PS filter paper and the solvent removed to give methyl 4-methoxy-2-(4-fluorophenyl)benzoate as a yellow-oily solid (7.2 g) which was used without further purification.

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 3.5 hours
  3. customresulting in a homogeneous solution
  4. customthe reaction was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 2N hydrochloric acid, water and brine
  6. filtrationfiltered through 1PS filter paper
  7. customthe solvent removed

Sources & evidence

ORD record
ord-13bb38d1e4df4201a20264da3bfffdc2
Source dataset
uspto-grants-2004_08
Patent number
US06777438B2

Reaction notes

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