Dimethyl Sulfoxide → Difluoro-4-chlorophenylacetaldehyde

HRID 54251노트

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HRID 54251 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:22])([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH2:13][OH:14].C(N(CC)CC)C>C(Cl)Cl.O>[F:22][C:12]([F:11])([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH:13]=[O:14]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 232378442-(4-Chlorophenyl)-2,2-difluoroethanol

생성물 1

HCID 23237846Difluoro-4-chlorophenylacetaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

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온도
-60 °C

실험 절차

A stirring solution of 7.0 grams (0.055 mole) of oxalyl chloride in 125 mL of methylene chloride is cooled to -60° C., and a solution of 9.5 grams (0.120 mole) of dimethyl sulfoxide in 25 mL of methylene chloride is added dropwise during a five minute period. Upon completion of addition, the reaction mixture is stirred at -60° C. for about 10 minutes, and then a solution of 9.6 grams (0.050 mole) of 2,2-difluoro-2-(4-chlorophenyl)ethanol in 25 mL of methylene chloride is added dropwise during a five minute period. Upon completion of addition, the reaction mixture is stirred for 15 minutes, and 25.5 grams (0.250 mole) of triethylamine is added while maintaining the reaction mixture temperature at -60° C. Upon completion of addition, the reaction mixture is allowed to warm to ambient temperature, and 150 mL of water is added. The mixture is stirred for 10 minutes, and the organic layer is separated. The aqueous layer is washed with 100 mL of methylene chloride. The methylene chloride wash and the organic layer are combined, and the combination is washed with 100 mL of water and then with 100 mL of an aqueous solution saturated with sodium chloride. The organic layer is dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding difluoro-4-chlorophenylacetaldehyde.

후처리

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. stirringthe reaction mixture is stirred for 15 minutes
  4. temperaturewhile maintaining the reaction mixture temperature at -60° C
  5. additionUpon completion of addition
  6. temperatureto warm to ambient temperature
  7. stirringThe mixture is stirred for 10 minutes
  8. customthe organic layer is separated
  9. washThe aqueous layer is washed with 100 mL of methylene chloride
  10. washThe methylene chloride wash
  11. washthe combination is washed with 100 mL of water
  12. dry with materialThe organic layer is dried with magnesium sulfate
  13. filtrationfiltered
  14. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-455472dbfeb14403985d8e7f20ff6fdc
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622954

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