Ethyl Acetate → 4-[4-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512577노트

반응식

HRID 512577 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=1.[Br:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([F:30])[CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1(C)C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O.CN(C)C=O>[Br:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][C:2]2[CH:7]=[CH:6][C:5]([CH:8]3[C:13](=[O:14])[C:12]([CH3:15])([CH3:16])[O:11][C:10]([CH3:17])([CH3:18])[C:9]3=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=2)=[C:25]([F:30])[CH:24]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27249814-Bromo-2-fluorophenolHCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

생성물 1

HCID 497654624-[4-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione

시약·촉매·용매 3

HCID 2734996copper(II) trifluoromethanesulfonate촉매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.42 g, 1.19 mmol), 4-bromo-2-fluorophenol (0.27 g, 1.43 mmol), cesium carbonate (0.78 g, 2.38 mmol), copper(II) trifluoromethanesulfonate (0.02 g, 0.06 mmol) and ethyl acetate (0.004 g, 0.06 mmol) in dry toluene (10 ml) are heated to reflux for 21 hours. The mixture is cooled to room temperature and N,N-dimethylformamide (2 ml) is added. The mixture is partitioned between 2M aqueous hydrochloric acid (10 ml) and ethyl acetate (3×10 ml). The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 4-[4-(4-bromo-2-fluorophenoxy)-2-ethylphenyl]-2,2,6,6-tetramethylpyran-3,5-dione.

후처리

  1. temperatureare heated
  2. temperatureto reflux for 21 hours
  3. customThe mixture is partitioned between 2M aqueous hydrochloric acid (10 ml) and ethyl acetate (3×10 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate evaporated under reduced pressure
  7. customThe residue is purified by preparative reverse phase HPLC

출처 및 근거

ORD 기록
ord-aeed1d6718e2428195b1570d221349db
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102642B2

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