Carbon Dioxide → 4-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid

HRID 405695노트

반응식

HRID 405695 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:25])[O:10][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH:12]=2)=[CH:4][C:3]=1[CH3:26].[Li]CCCC.[C:32](=[O:34])=[O:33].Cl>C1COCC1.CCCCCC.CCOCC>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]([CH3:25])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:32]([OH:34])=[O:33])=[C:3]([CH3:26])[CH:4]=3)=[CH:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 533734923-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazoleHCID 178418339Butyllithium

생성물 1

HCID 533715064-[5-(3,5-Dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-90 °C

실험 절차

210 mg of 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-2-methyl-5-trifluoromethyl-2,5-dihydro-isoxazole (IIIa) was dissolved in 20 ml of dry THF, cooled to −90° C. and treated with 0.625 ml BuLi 1.6M in hexane. The mixture was stirred for 1 hour at −80° C. and then a great excess of solid CO2 was added to the mixture. The temperature was allowed to rise up to −30° C. (1 hour) and 5 ml of 1M HCl was added followed with ether. The organic layer was dried and evaporated to dryness. The residual resin was used in the final step without purification.

후처리

  1. customto rise up to −30° C.
  2. additionwas added
  3. customThe organic layer was dried
  4. customevaporated to dryness
  5. customwithout purification

출처 및 근거

ORD 기록
ord-4a29bd076f6c40468825e3149c213de9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754053B2

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