反応 #57948

反応方程式

2-(3,5-bis-trifluoromethyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester

1,3-dibromopropane

potassium carbonate

→

2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester

収率 78.0%

溶媒

acetone

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度to reflux for 3 hours
3. 3
   その他The mixture was partitioned between ethyl acetate and brine
4. 4
   その他the layers were separated
5. 5
   抽出The aqueous layer was extracted with one additional portion of ethyl acetate
6. 6
   洗浄washed with one portion of brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他The crude oil was purified by flash chromatography through silica gel

実験手順

To a solution of 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-hydroxy-benzoic acid methyl ester (10.10 g, 2.70 mmol) and 1,3-dibromopropane (2.18 g, 10.8 mmol) in acetone (75 mL) was added potassium carbonate (1.87 g, 13.5 mmol). The reaction mixture was heated to reflux for 3 hours and allowed to cool back down to room temperature. The mixture was partitioned between ethyl acetate and brine, and the layers were separated. The aqueous layer was extracted with one additional portion of ethyl acetate. The organics were combined, washed with one portion of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 8/92) to give 2-(3,5-bis-trifluoromethyl-benzoylamino)-4-(3-bromo-propoxy)-benzoic acid methyl ester (1.11 g, 78%) as a white powder. 1H NMR (400 MHz, CDCl3); δ 12.58 (s, 1H), 8.53 (d, 1H), 8.51 (s, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 6.70 (dd, 1H), 4.24 (t, 2H), 3.96 (s, 3H), 3.62 (t, 2H), 2.37 (m, 2H).

出典