Reaktion #2353441

Reaktionsgleichung

1-bromo-3-fluoro-2-iodo-benzene

Na2CO3

3-methyl phenylboronic acid

→

6-bromo-2-fluoro-3′-methyl-biphenyl

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was heated
2. 2
   Temperaturat reflux under N2 for 12 h
3. 3
   SonstigeThe mixture was partitioned between water and EtOAc
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigepurified by column chromatography

Vorschrift

Pd(Ph3P)4 in a 500-mL round-bottom flask under N2 atmosphere was treated sequentially with a solution of 1-bromo-3-fluoro-2-iodo-benzene (30 g, 0.1 mol) in toluene (250 mL), a solution of 2N aq Na2CO3 (200 mL) and 3-methyl phenylboronic acid in ethanol (62 mL). This mixture was heated at reflux under N2 for 12 h, then cooled to rt. The mixture was partitioned between water and EtOAc. The combined organic layers were washed with brine, dried over MgSO4, evaporated and purified by column chromatography to give 6-bromo-2-fluoro-3′-methyl-biphenyl (12 g). 1H NMR (400 MHz, CD3OD): 7.03 (m, 2H), 7.48-7.04 (m, 4H), 7.50 (d, 1H).

Quelle