تفاعل #9654

معادلة التفاعل

4-acetyl-3-methylphenyl trifluoromethanesulfonate

4-nitrophenylboronic acid

sodium carbonate

dioxane

→

1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone

المردود 99.9%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   أخرىThe layers were separated
3. 3
   غسيلthe organic layer was washed with water (2×50 mL)
4. 4
   تجفيفdried over magnesium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   أخرىto give a dark brown oil
7. 7
   أخرىThis material was purified by flash chromatography (7 to 20% ethyl acetate/hexane)

الإجراء التجريبي

A mixture of 4-acetyl-3-methylphenyl trifluoromethanesulfonate (6.90 g, 24.0 mmol), 4-nitrophenylboronic acid (3.80 g, 24 mmol), 2 N aqueous sodium carbonate (88.0 mL), dioxane (88.0 mL), and toluene (296 mL) was purged with argon for 30 minutes before [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1 complex with dichloromethane, 1.90 g, 2.30 mmol) was added. The reaction mixture was heated at 85° C. and stirred overnight. The layers were separated and the organic layer was washed with water (2×50 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give a dark brown oil. This material was purified by flash chromatography (7 to 20% ethyl acetate/hexane) to give 1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone as a light yellow solid (6.12 g, 99% yield). GC-MS m/z 255 (M+), ret. time 9.89 min; 1H NMR (CDCl3) δ: 2.61 (s, 3H), 2.62 (s, 3H), 7.49–55 (m, 2H), 7.78 (d, 2H), 7.81 (d, 1H), 8.32 (d, 2H).

المصدر