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

HRID 1773545노트

반응식

HRID 1773545 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 14528105Methyl 7-bromo-3-methoxy-2-naphthoate수율 101.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ff97dfdd19254c0c8b1c4f097a62a479
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255110B2

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