تفاعل #63969

معادلة التفاعل

1,2-dibromotetrafluoroethane

2-chloro-4-nitrophenol

potassium carbonate

sodium hydroxide

propanethiol

→

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

المردود 190.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe pressure bottle was sealed
2. 2
   درجة الحرارةThe pressure bottle was cooled to room temperature
3. 3
   workup.ADDITIONthe contents poured into a separatory funnel
4. 4
   استخلاصThe resultant mixture was extracted with four 300 mL portions of diethyl ether
5. 5
   غسيلwashed with two 100 mL portions of a 2N sodium hydroxide solution
6. 6
   استخلاصThe washed extract
7. 7
   تجفيفwas dried over anhydrous magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىThe filtrate was evaporated under reduced pressure
10. 10
    أخرىleaving an oil
11. 11
    أخرىpurified by column chromatography on silica gel
12. 12
    غسيلeluting with n-heptane:toluene (95:5)

الإجراء التجريبي

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.

المصدر