Water → 2-(2,6-Dibromo-pyridin-4-yloxy)-4-fluoro-benzoic acid methyl ester

HRID 1848920노트

반응식

HRID 1848920 반응식
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[Br:13][C:14]1[CH:19]=[C:18]([N+]([O-])=O)[CH:17]=[C:16]([Br:23])[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=1[O:12][C:18]1[CH:17]=[C:16]([Br:23])[N:15]=[C:14]([Br:13])[CH:19]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2775386Methyl 4-fluorosalicylateHCID 160387482,6-Dibromo-4-nitropyridine

생성물 1

HCID 866428782-(2,6-Dibromo-pyridin-4-yloxy)-4-fluoro-benzoic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of methyl 4-fluoro-2-hydroxybenzoate (2.00 g), 2,6-dibromo-4-nitropyridine (3.65 g), and cesium carbonate (4.21 g) in N,N-dimethylformamide (100 mL) was heated to 55° C. for 16 hours, cooled, added to water, and extracted with 50% ethyl acetate in hexanes. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography on silica gel using 30-50% ethyl acetate in hexanes.

후처리

  1. temperaturecooled
  2. extractionextracted with 50% ethyl acetate in hexanes
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography on silica gel using 30-50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-442f7271587641c594b49147de302eba
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952157B2

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