Dimethyl Sulfate → Methyl 7-bromo-3-methoxy-2-naphthoate

HRID 1773545ノート

反応式

HRID 1773545 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](O)[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[K+].[K+].COS([O:27][CH3:28])(=O)=O>CC(C)=O>[CH3:16][O:14][C:12]([C:8]1[C:7]([O:27][CH3:28])=[CH:6][C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:9]=1)=[O:13]

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-

生成物 1

HCID 14528105Methyl 7-bromo-3-methoxy-2-naphthoate収率 101.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 7-bromo-3-hydroxy-naphthalene-2-carboxylic acid (J. Med. Chem. 1990, 33(1), 171) (5.3 g, 19.85 mmol), potassium carbonate (13.7 g, 99.25 mmol) and dimethylsulfate (3.8 mL, 45.66 mmol) in acetone (50 mL) was heated at reflux for 3.5 hours. The reaction mixture was then filtered; the filtrate was treated with water (5 mL) and the resulting mixture was stirred for 10 minutes. The reaction mixture was concentrated under reduced pressure; the residue was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 5.946 g of 7-bromo-3-methoxy-naphthalene-2-carboxylic acid methyl ester without further purifications.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 hours
  3. filtrationThe reaction mixture was then filtered
  4. additionthe filtrate was treated with water (5 mL)
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. dissolutionthe residue was dissolved in dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-ff97dfdd19254c0c8b1c4f097a62a479
出典データセット
uspto-grants-2016_02
特許番号
US09255110B2

反応ノート

読み込み中…