Methanol → 4-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acid

HRID 69396노트

반응식

HRID 69396 반응식
C([O:3][C:4](=[O:30])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]([Br:16])[C:14]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:13][N:12]=2)=[CH:7][C:6]=1[CH3:29])C.O.[OH-].[Li+].CO>O>[Br:16][CH:15]1[C:14]([C:21]2[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=2)([C:17]([F:18])([F:19])[F:20])[O:13][N:12]=[C:11]1[C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:30])=[O:3])=[C:6]([CH3:29])[CH:7]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 866551484-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester

생성물 1

HCID 866551474-[4-Bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acid수율 88%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 4-[4-bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester (0.71 g, 1.35 mmol) (Example 1.6), lithium hydroxide monohydrate (0.17 g, 4 mmol), methanol (25 ml) and water (5 ml) was stirred at ambient temperature for 60 hours. The mixture was concentrated and the residue dissolved in water. The solution was acidified by addition of aqueous hydrochloric acid (1N). The precipitate was isolated by filtration and dried under vacuum to afford 4-[4-bromo-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-benzoic acid (0.59 g, 88% yield) as a white powder. 1H-NMR (CDCl3, 400 MHz): 8.05-7.45 (m, 6H), 5.87 (s, 1H), 2.65 (s, 3H) ppm.

후처리

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue dissolved in water
  3. additionThe solution was acidified by addition of aqueous hydrochloric acid (1N)
  4. customThe precipitate was isolated by filtration
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-e2c8185aced54ac89e8c7a80aed00b8b
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822502B2

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