2-Bromopropane → Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

HRID 1964118노트

반응식

HRID 1964118 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15](=O)([O-])[O-].[Cs+].[Cs+].Br[CH:22]([CH3:24])[CH3:23].[CH3:25][C:26](N(C)C)=O>>[CH:22]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH:26]([CH3:25])[CH3:15])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14])([CH3:24])[CH3:23]

참가 물질

5

반응물 4

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

생성물 1

HCID 59201795Isopropyl 4-isopropoxy-3-(trifluoromethyl)benzoate

반응 조건

온도
80 °C

실험 절차

To a mixture of 4-hydroxy-3-(trifluoromethyl)benzoic acid (14.55 mmol) and cesium carbonate (43.7 mmol) in DMA (60 mL) was added 2-bromopropane (36.4 mmol). The reaction was stirred at 80° C. for 16 h. The mixture was filtered through celite and concentrated under vacuum. The residue was dissolved in EtOAc and washed with water, then brine, then dried over MgSO4, and filtered. The solvent was removed under vacuum to give the title compound as a light yellow oil (13.1 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.36 (d, J=6.32 Hz, 6H), 1.39 (d, J=6.06 Hz, 6H), 4.72 (septet, J=6.06 Hz, 1H), 5.24 (septet, J=6.25 Hz, 1H), 7.00 (d, J=8.84 Hz, 1H), 7.26 (s, OH), 8.15 (dd, J=8.72, 2.15 Hz, 1H), 8.23 (d, J=2.15 Hz, 1H).

후처리

  1. filtrationThe mixture was filtered through celite
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water
  5. dry with materialbrine, then dried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-8f20c318bf5846dc82cf8e227c45570d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415484B2

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