反応 #45583

反応方程式

(2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide 4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate

p-toluenesulfonic acid monohydrate

toluene

→

compound

収率 85.7%

7-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

収率 85.7%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 1.5 hours
3. 3
   温度After cooling
4. 4
   その他the reaction liquid
5. 5
   洗浄successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
6. 6
   乾燥dried on anhydrous magnesium sulfate
7. 7
   その他the solvent was evaporated away under reduced pressure
8. 8
   その他to obtain a pale brown residue
9. 9
   その他The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

実験手順

Next, a mixture of (2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide/4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate mixture (160 mg, 0.426 mmol), p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol) and toluene (13 ml) was heated under reflux for 1.5 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (129 mg) as a colorless solid.

出典