Cesium carbonate → 3-(2-Bromo-pyridin-4-yloxy)-benzoic acid

HRID 521758

反応式

HRID 521758 の反応式
[Br:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C[O:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CS(C)=O.C(OCC)(=O)C.CO.O>[Br:1][C:2]1[CH:7]=[C:6]([O:18][C:14]2[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=2)[C:11]([OH:19])=[O:10])[CH:5]=[CH:4][N:3]=1

参加物

9

反応物 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 88068Methyl 3-HydroxybenzoateHCID 27628362-Bromo-4-chloropyridine

生成物 1

HCID 581679363-(2-Bromo-pyridin-4-yloxy)-benzoic acid

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
66 °C

実験手順

A mixture of 2-bromo-4-chloro-pyridine (200 mg, 1.04 mmol), methyl-3-hydroxybenzoate (158 mg, 1.04 mmol), cesium carbonate (507 mg, 1.56 mmol) in 10 ml of anhydrous DMSO was heated at 66° C. for 5 hours. The mixture was diluted with ethyl acetate (100 ml), washed with brine (3×50 ml), dried over Na2SO4 and evaporated to give a colorless oil. The oil was dissolved in MeOH (8 ml), and 2M NaOH solution (4 ml, 8 mmol) was added. The mixture was heated at 60° C. for 20 minutes, poured into 50 ml of water, and acidified to pH=4. The precipitates were filtered, washed with water and dried in vacuo to give 3-(2-bromo-pyridin-4-yloxy)-benzoic acid as white solid. Yield: 170 mg, 56%.

後処理

  1. washwashed with brine (3×50 ml)
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customto give a colorless oil
  5. temperatureThe mixture was heated at 60° C. for 20 minutes
  6. filtrationThe precipitates were filtered
  7. washwashed with water
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-f29c056ee6d54b999a20a8210d7db75c
出典データセット
uspto-grants-2016_05
特許番号
US09328103B2

関連ノート

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