反応 #76350

反応方程式

3-Aminophenol

4-bromo-α,α,α-trifluorotoluene

cesium carbonate

→

3-(4-trifluoromethylphenoxy)aniline

収率 59.0%

溶媒

dimethylacetamide

water

反応条件

後処理

1. 1
   抽出the aqueous layer was extracted with diethyl ether (4×60 mL)
2. 2
   洗浄The combined ether layers were washed with 3% HCl, 5% NaOH and water
3. 3
   乾燥dried over anhydrous MgSO4
4. 4
   その他The ether was removed in vacuo
5. 5
   その他the recovered oil purified by flash column chromatography on silica gel eluting with ethyl acetate in hexane (1:8)

実験手順

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.

出典