반응 #2186179

반응 방정식

sulfuric acid

3-chloro-2-fluoroaniline

sulfuric acid

sodium nitrite

→

3-chloro-2-fluorophenol

수율 40.9%

용매

toluene

반응 조건

후처리

1. 1
   온도Thereafter, the mixture was cooled to −10° C.
2. 2
   workup.WAITover 90 minutes in a temperature range of −10 to −5° C.
3. 3
   workup.STIRRINGby stirring for 30 minutes in that temperature range
4. 4
   기타The resulting reaction mixture
5. 5
   workup.ADDITIONwas added to another reactor
6. 6
   workup.WAITover 6 hours in a temperature range of 80 to 85° C.
7. 7
   workup.STIRRINGby stirring for 30 minutes in that temperature range
8. 8
   기타The resulting reaction mixture
9. 9
   온도was cooled to a temperature range of 70 to 75° C.
10. 10
    workup.WAITleft at rest
11. 11
    기타to separate into two layers, i.e.
12. 12
    기타an organic layer and an aqueous layer, and the organic layer was collected
13. 13
    온도The aqueous layer was cooled to 20° C.
14. 14
    여과copper sulfate was filtered off
15. 15
    추출by extracting with 1,200 mL toluene twice
16. 16
    기타The organic layer obtained by extraction
17. 17
    세척was washed with 700 mL of water
18. 18
    workup.DISTILLATIONsubjected to fractional distillation

실험 절차

728 g of 3-chloro-2-fluoroaniline was added to a reactor having 6,860 g of 30.6% sulfuric acid placed therein, followed by stirring for 30 minutes at 80° C. Thereafter, the mixture was cooled to −10° C., and 952 g of a 37.0% sodium nitrite aqueous solution was added dropwise thereto over 90 minutes in a temperature range of −10 to −5° C., followed by stirring for 30 minutes in that temperature range. The resulting reaction mixture was added to another reactor having 4,100 g of 51.2% sulfuric acid, 1,500 g of copper sulfate and 3,000 mL of toluene placed therein over 6 hours in a temperature range of 80 to 85° C., followed by stirring for 30 minutes in that temperature range. The resulting reaction mixture was cooled to a temperature range of 70 to 75° C. and left at rest to separate into two layers, i.e., an organic layer and an aqueous layer, and the organic layer was collected. The aqueous layer was cooled to 20° C., and copper sulfate was filtered off, followed by extracting with 1,200 mL toluene twice. The organic layer obtained by extraction was washed with 700 mL of water and subjected to fractional distillation to obtain 300 g of 3-chloro-2-fluorophenol (b5). The compound had a boiling point of 60 to 62° C./1 mmHg.

출처