3-(Trifluoromethyl)phenol → Halofenate

HRID 2192707노트

반응식

HRID 2192707 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].Br[CH:15]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])=[O:17].C(O)(C)C.[O-]C1C=CC=CC=1>C(O)(C)C>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:15]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[CH:3]=2)[C:16]([O:18][CH2:19][CH2:20][NH:21][C:22](=[O:24])[CH3:23])=[O:17])=[CH:26][CH:27]=1

참가 물질

6

반응물 4

HCID 73763-(Trifluoromethyl)phenolHCID 14797Potassium HydroxideHCID 220253142-(Acetylamino)ethyl α-bromo-4-chlorobenzeneacetateHCID 131724051HCID 131724051, 화합물

생성물 1

HCID 33584Halofenate

시약·촉매·용매 1

HCID 3776Isopropanol용매2회

실험 절차

3-Hydroxybenzotrifluoride was added to a solution of potassium hydroxide in isopropanol. N-acetylaminoethyl 2-bromo-2-(4-chlorophenyl)acetate in isopropanol was added to the isopropanol/phenoxide solution and stirred at room temperature for 4 hours. The isopropanol was removed by vacuum distillation, and the resulting slush was dissolved in ethyl acetate and washed twice with water and once with brine. After drying over magnesium sulfate and filtration, the solvent was removed to give crude product as an oil. The crude product was dissolved in hot toluene/hexanes (1:1 v/v) and cooled to between 0 and 10° C. to crystallize the product. The filter cake was washed with hexanes/toluene (1:1 v/v) and then dried under vacuum at 50° C. The isolated solid was dissolved in hot 1:6 (v/v) isopropanol in hexanes. After cooling, the pure racemic 2-Acetamidoethyl 4-Chlorophenyl-(3-trifluoro methylphenoxy)-acetate formed as a crystalline solid. The solid was collected by filtration, the filter cake washed with 1:6 (v/v) isopropanol in hexanes and dried under vacuum at 50° C.

후처리

  1. customThe isopropanol was removed by vacuum distillation
  2. dissolutionthe resulting slush was dissolved in ethyl acetate
  3. washwashed twice with water and once with brine
  4. dry with materialAfter drying over magnesium sulfate and filtration
  5. customthe solvent was removed
  6. customto give crude product as an oil
  7. temperaturecooled to between 0 and 10° C.
  8. customto crystallize the product
  9. washThe filter cake was washed with hexanes/toluene (1:1 v/v)
  10. customdried under vacuum at 50° C
  11. dissolutionThe isolated solid was dissolved in hot 1:6 (v/v) isopropanol in hexanes
  12. temperatureAfter cooling

출처 및 근거

ORD 기록
ord-324ee79c5ce3454cbd031f0795d54f48
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329749B2

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