Reaktion #1002809

Reaktionsgleichung

triphenylphosphine

methyl-4-bromobenzoate

2-chlorophenylboronic acid

sodium carbonate

→

2′-chlorobiphenyl-4-carboxylic acid methyl ester

Lösungsmittel

ethyl acetate

dimethylformamide

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurge the reaction mixture with argon
2. 2
   Sonstigepurge again with argon
3. 3
   Sonstigethe sealed reaction in an oil bath
4. 4
   TemperaturCool
5. 5
   Sonstigethe reaction to room temperature
6. 6
   Filtrationfilter through a short plug of celite with additional ethyl acetate
7. 7
   WaschenWash the organics with water
8. 8
   Trocknendry over magnesium sulfate
9. 9
   Filtrationfilter
10. 10
    Sonstigeevaporate
11. 11
    SonstigePurification by flash column chromatography

Vorschrift

Combine methyl-4-bromobenzoate (1.0 g, 4.65 mmol), 2-chlorophenylboronic acid (799 mg, 5.1 mmol), Pd(OAc)2 (51 mg, 0.46 mmol) and sodium carbonate (1.5 g, 13.9 mmol) in dimethylformamide (20 mL) and water (2.0 mL) with stirring. Purge the reaction mixture with argon, add triphenylphosphine (61 mg, 0.23 mmol) and purge again with argon. Place the sealed reaction in an oil bath maintained at 80° C. and allow to stir for 1 hour. Cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over magnesium sulfate, filter and evaporate. Purification by flash column chromatography yields 2′-chlorobiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in tetrahydrofuran (0.25M) and add an equal volume of 1M sodium hydroxide. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCl and extract with ethyl acetate. Evaporation of the solvent yields 762 mg (67%) of the title compound. MS (m/e): 231.1 (M−).

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