反応 #63969

反応方程式

1,2-dibromotetrafluoroethane

2-chloro-4-nitrophenol

potassium carbonate

sodium hydroxide

propanethiol

→

3-chloro4-(2-bromo-1,1,2,2-tetrafluoroethoxy)nitrobenzene

収率 190.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他The pressure bottle was sealed
2. 2
   温度The pressure bottle was cooled to room temperature
3. 3
   workup.ADDITIONthe contents poured into a separatory funnel
4. 4
   抽出The resultant mixture was extracted with four 300 mL portions of diethyl ether
5. 5
   洗浄washed with two 100 mL portions of a 2N sodium hydroxide solution
6. 6
   抽出The washed extract
7. 7
   乾燥was dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   その他The filtrate was evaporated under reduced pressure
10. 10
    その他leaving an oil
11. 11
    その他purified by column chromatography on silica gel
12. 12
    洗浄eluting with n-heptane:toluene (95:5)

実験手順

Into a pressure bottle was placed 15.0 g (0.086 mole) 2-chloro-4-nitrophenol, 11.9 g (0.086 mole) potassium carbonate, 1.5 g (0.02 mole) propanethiol, 33.7 g (0.13 mole) 1,2-dibromotetrafluoroethane and 115 mL of N,N-dimethylformamide. The pressure bottle was sealed and the mixture stirred at 50° C. for 48 hours. The pressure bottle was cooled to room temperature, opened, and the contents poured into a separatory funnel. Approximately 200 mL of a 2N sodium hydroxide solution was added to the separatory funnel. The resultant mixture was extracted with four 300 mL portions of diethyl ether. The extracts were combined and washed with two 100 mL portions of a 2N sodium hydroxide solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure leaving an oil. The reaction described above was repeated three additional times. The residual oils from the four experiments were combined and purified by column chromatography on silica gel, eluting with n-heptane:toluene (95:5), to yield 57.6 g of 3-chloro4-(2-bromo-1,1,2,2-tetrafluoroethoxy)nitrobenzene as an oil.

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