Triethylamine → 4-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

HRID 1037018노트

반응식

HRID 1037018 반응식
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=1.[Cl:15][C:16]1[CH:21]=[C:20]([C:22]([C:24]([F:27])([F:26])[F:25])=[CH2:23])[CH:19]=[C:18]([Cl:28])[C:17]=1[F:29].CCN(CC)CC.CC(=O)OCC>CN(C=O)C.CC(=O)OCC.CO>[Cl:15][C:16]1[CH:21]=[C:20]([C:22]2([C:24]([F:27])([F:26])[F:25])[O:14][N:13]=[C:2]([C:3]3[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([CH3:12])[CH:4]=3)[CH2:23]2)[CH:19]=[C:18]([Cl:28])[C:17]=1[F:29]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 584682331,3-Dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86685466HCID 86685466, 화합물

생성물 1

HCID 866854534-(5-(3,5-Dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid수율 58%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584119Ethylacetate methanol용매

실험 절차

To a solution of 4-(chloro(hydroxyimino)methyl)-2-methylbenzoic acid (5.1 g, 23.8 mmol) in DMF (30 mL) at 0° C. was added 1,3-dichloro-2-fluoro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (7.4 g, 28.6 mmol) followed by Et3N (4.8 g, 47.6 mmol). The reaction mixture was stirred at rt for 18 h, poured into ice-water (30 mL) and extracted with ethyl acetate (60 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (1:1) to EA: MeOH (10:1) to give 4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid (6 g; yield 58% over 3 steps) as a white solid. MS: m/z=435.8 (M+1, ESI+).

후처리

  1. extractionextracted with ethyl acetate (60 mL×3)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel
  7. washeluted with PE

출처 및 근거

ORD 기록
ord-abe7fcca9e1941a1bbb37ef27692846f
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546357B2

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