Reaktion #1530518

Reaktionsgleichung

dichloromethane

Na2CO3

3-methyl benzene boronic acid

(6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone

→

yellow solid

Ausbeute 69.3%

(2,4-Dichloro-phenyl)-(3-methyl-6-m-tolyl-benzofuran-2-yl)-methanone

Ausbeute 69.3%

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was bubbled with argon for another 5 min
2. 2
   workup.ADDITIONThe reaction was diluted with ethyl acetate
3. 3
   Waschenwashed with water, brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeThe solvent was removed at reduced pressure
6. 6
   Sonstigepurified on the pre-HPLC

Vorschrift

A solution of (6-Bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (50 mg, 0.13 mmol) in toluene (1.5 mL) and ethanol (1.5 mL) was degassed with argon for 15 min. At this time, 3-methyl benzene boronic acid (21.2 mg, 0.16 mmol, 1.2 eq) was added followed by [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II), complex with dichloromethane (1:1) (10.6 mg, 0.01 mmol, 0.1 eq) and 2M aqueous Na2CO3 (0.21 mL, 3 eq). The reaction was bubbled with argon for another 5 min and then heated to 85° C. for 4 h. The reaction was diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. The solvent was removed at reduced pressure and purified on the pre-HPLC to afford 35.6 mg (69%) of a yellow solid as the product. 1H-NMR (CDCl3): δ 7.72 (d, J=8.0 Hz, 1H), 7.65 (s, 1H), 7.57 (dd, J=1.6, 8.0 Hz, 1H), 7.50 (d, J=1.9 Hz, 1H), 7.58 to 7.53 (m, 4H), 7.33 (t, 1H), 7.18 (d, J=7.2 Hz, 1H), 2.56 (s, 3H), 2.42 (s, 3H); LC-MS (MH+=395/397).

Quelle