反応 #2487010

反応方程式

2-fluorophenylacetonitrile

sodium hydroxide

sodium hydroxide

2-bromopropane

→

compound

収率 71.2%

2-fluoro-α-(1-methylethyl)benzeneacetonitrile

収率 71.2%

反応条件

後処理

1. 1
   温度The temperature was increased to 90°-95
2. 2
   温度so maintained for 1.0 hour
3. 3
   温度After cooling
4. 4
   その他the mixture was partitioned between diethyl ether and water
5. 5
   洗浄The organic layer was washed with brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   その他the solvent evaporated

実験手順

A mixture of 2-fluorophenylacetonitrile (10.0 g, 74.1 mmoles), 50% aqueous sodium hydroxide (5.2 g), sodium hydroxide (741 mg), tetra-n-butylammonium chloride (3.3 g), and 2-bromopropane (10.0 g, 81.5 mmoles) was stirred rapidly while heating from room temperature to 60°-65°. The temperature was increased to 90°-95 and so maintained for 1.0 hour. After cooling, the mixture was partitioned between diethyl ether and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and the solvent evaporated. Chromatography of the residue over silica gel using 30% methylene chloride-hexane as eluent gave a compound (9.35 g) as a water-white oil which was characterized by NMR, as follows: 1H NMR(CDCl3) d 7.51-7.00 (m, 4H), 3.99 (d, 1H), 2.22 (m, 1H), 1.06 (d, 1H).

出典