تفاعل #45312

معادلة التفاعل

methyl [3,5-bis(trifluoromethyl)benzyl][2-iodo-5-(trifluoromethyl)benzyl]carbamate

2-methoxy-5-methylphenyl boronic acid

potassium carbonate

→

title compound

Methyl [3,5-bis(trifluoromethyl)benzyl]{[2′-methoxy-5′-methyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

المذيبات

acetone water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةmaintained
3. 3
   درجة الحرارةat reflux for 1 h
4. 4
   أخرىAcetone was removed
5. 5
   استخلاصthe residue was extracted with methylene chloride (3×10 ml)
6. 6
   غسيلThe combined organic layers were washed with water
7. 7
   تجفيفbrine, and dried over sodium sulfate

الإجراء التجريبي

A mixture of methyl [3,5-bis(trifluoromethyl)benzyl][2-iodo-5-(trifluoromethyl)benzyl]carbamate (0.10 g, 0.17 mmol) from Example 5, and 2-methoxy-5-methylphenyl boronic acid (0.034 g, 0.2 mmol), palladium acetate (0.0038 g, 0.017 mmol) and potassium carbonate (0.047 g, 0.34 mmol) in 4:1 acetone/water (10 ml) was heated and maintained at reflux for 1 h. The color of the solution turned dark. Acetone was removed and the residue was extracted with methylene chloride (3×10 ml). The combined organic layers were washed with water, then brine, and dried over sodium sulfate. The title compound was obtained as a colorless oil by preparative thin layer chromatography using acetone/hexane (5:95) as the eluant. 1H NMR (CDCl3, 500 MHz): δ 7.73 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.47 (s, 2H), 7.35 (m, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.19 (m, 1H), 6.85 (m, 2H), 4.23-4.36 (m, 4H), 3.79 (m, 3H), 3.68 (s, 3H), 2.25 (s, 3H). LC-MS (M+1): 580.0 (4.61 min).

المصدر