反応 #315069

反応方程式

4-Bromo-benzoic acid methyl ester

2,4-Dichloro-phenyl boronic acid

Na2CO3

→

title compound

2′,4′-Dichloro-biphenyl-4-carboxylic acid methyl ester

溶媒

toluene

ethanol

反応条件

後処理

1. 1
   温度The mixture was refluxed
2. 2
   workup.STIRRINGwith stirring for 3 hours under an atmosphere of N2
3. 3
   その他The solvent was removed under vacuum
4. 4
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
5. 5
   洗浄washed with water and saturated NaCl solution
6. 6
   乾燥After drying (Na2SO4)
7. 7
   その他the solvent was evaporated
8. 8
   その他the resultant oil purified by column chromatography
9. 9
   その他to give a fluffy white powder, which
10. 10
    その他was recrystallised from ethanol

実験手順

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).

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