3-(Trifluoromethyl)phenol → Halofenate

HRID 2064568ノート

反応式

HRID 2064568 の反応式
[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

参加物

6

反応物 4

HCID 73763-(Trifluoromethyl)phenolHCID 14797Potassium HydroxideHCID 220253142-(Acetylamino)ethyl α-bromo-4-chlorobenzeneacetateHCID 131724051HCID 131724051、化合物

生成物 1

HCID 33584Halofenate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19c834343e714aab84e29c1b3542f07a
出典データセット
uspto-grants-2012_10
特許番号
US08288438B2

反応ノート

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