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

HRID 1848920ノート

反応式

HRID 1848920 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-442f7271587641c594b49147de302eba
出典データセット
uspto-grants-2015_02
特許番号
US08952157B2

反応ノート

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