反応 #2186179

反応方程式

sulfuric acid

3-chloro-2-fluoroaniline

sulfuric acid

sodium nitrite

→

3-chloro-2-fluorophenol

収率 40.9%

溶媒

toluene

反応条件

後処理

1. 1
   温度Thereafter, 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
   その他The 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
   その他The resulting reaction mixture
9. 9
   温度was cooled to a temperature range of 70 to 75° C.
10. 10
    workup.WAITleft at rest
11. 11
    その他to separate into two layers, i.e.
12. 12
    その他an organic layer and an aqueous layer, and the organic layer was collected
13. 13
    温度The aqueous layer was cooled to 20° C.
14. 14
    ろ過copper sulfate was filtered off
15. 15
    抽出by extracting with 1,200 mL toluene twice
16. 16
    その他The organic layer obtained by extraction
17. 17
    洗浄was washed with 700 mL of water
18. 18
    workup.DISTILLATIONsubjected to fractional distillation

実験手順

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.

出典