تفاعل #76350

معادلة التفاعل

3-Aminophenol

4-bromo-α,α,α-trifluorotoluene

cesium carbonate

→

3-(4-trifluoromethylphenoxy)aniline

المردود 59.0%

المذيبات

dimethylacetamide

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصthe aqueous layer was extracted with diethyl ether (4×60 mL)
2. 2
   غسيلThe combined ether layers were washed with 3% HCl, 5% NaOH and water
3. 3
   تجفيفdried over anhydrous MgSO4
4. 4
   أخرىThe ether was removed in vacuo
5. 5
   أخرىthe recovered oil purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8)

الإجراء التجريبي

Ex-656A) 3-Aminophenol (5.0 g, 45.8 mmol) and 4-bromo-α,α,α-trifluorotoluene (14.0 g, 62.2 mmol) were dissolved in anhydrous dimethylacetamide (20 mL), then anhydrous cesium carbonate (30 g, 92.3 mmol) and copper triflate benzene complex (200 mg) were added. The mixture was stirred and heated to 85° C. using a reflux condenser under an argon atmosphere. After 16 h, the mixture was diluted with water (120 mL), and the aqueous layer was extracted with diethyl ether (4×60 mL). The combined ether layers were washed with 3% HCl, 5% NaOH and water, then dried over anhydrous MgSO4. The ether was removed in vacuo, and the recovered oil purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8) to give 6.8 g (59%) of the desired 3-(4-trifluoromethylphenoxy)aniline product as a yellow oil, which solidified to a yellow powder, 98% pure by HPLC analysis. HRMS calcd. for C13H10F3NO: 254.0792 [M+H]+, found: 254.0798.

المصدر