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Ethyl chloroformate → Ethyl 2,6-dichloro-4-(trifluoromethyl)benzoate

HRID 1288716
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HRID 1288716 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1Br.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21].[Cl-].[NH4+]>CCOCC>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:8]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]
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참가 물질

6

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HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 12682564-Bromo-3,5-dichlorobenzotrifluorideHCID 178418339Butyllithium

생성물 1

HCID 54315306Ethyl 2,6-dichloro-4-(trifluoromethyl)benzoate수율 77.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether
용매

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온도
-78 °C

실험 절차

n-Butyllithium (1.6M in hexane, 330 ml) was added dropwise with stirring to a solution of 2,6-dichloro-4-trifluoromethylbromobenzene (163.3 g) in ether while maintaining the temperature below -70° C. The mixture was stirred for 1 hour at -78° C. then ethyl chloroformate (61.7 g) was added while maintaining the temperature below -70° C. The mixture was stirred at room temperature overnight. It was cooled to 0° C. and a saturated aqueous solution of ammonium chloride was added. The layers were separated and the organic layer was washed with water, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give ethyl 2,6-dichloro-4-trifluoromethylbenzoate (123.9 g) as a colourless liquid bp 90°-96° C. at 5 mmHg.

후처리

  1. temperaturewhile maintaining the temperature below -70° C
  2. temperaturewhile maintaining the temperature below -70° C
  3. stirringThe mixture was stirred at room temperature overnight
  4. temperatureIt was cooled to 0° C.
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customThe filtrate was evaporated to dryness
  10. distillationthe residue was distilled

출처 및 근거

ORD 기록
ord-825cef61c5cc4ab9a371de940b3a9004
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05747424

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