Methyl iodide → 4-Bromo-2-butyl-6-fluoro-5-methoxy-1-indanone

HRID 7890노트

반응식

HRID 7890 반응식
[Br:1][C:2]1[C:10]([OH:11])=[C:9]([F:12])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]2=[O:13].CI.[C:20](=O)(O)[O-].[Na+]>CN(C)C=O>[Br:1][C:2]1[C:10]([O:11][CH3:20])=[C:9]([F:12])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]2=[O:13]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 219908524-Bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone

생성물 1

HCID 219909064-Bromo-2-butyl-6-fluoro-5-methoxy-1-indanone수율 81.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-bromo-2-butyl-6-fluoro-5-hydroxy-1-indanone (2.17 g, 7.23 mmol), N,N-dimethylformamide (14.5 mL), methyl iodide (0.675 mL, 10.84 mmol), and sodium bicarbonate (1.50 g, 18.1 mmol) was stirred at room temperature for 17 hours. The solvent was evaporated under vacuum. The residue in EtOAc (150 mL) was washed with water (5×100 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (2.29 g). The crude product was dissolved in CH2CL2 (5 mL) and the solution filtered through a pad of EM silica gel 60 (20 mL) using an additional 60 mL of CH2Cl2 to elute the silica gel. The CH2Cl2 filtrate was evaporated under vacuum to afford 4-bromo-2-butyl-6-fluoro-5-methoxy-1-indanone (1.86 g) as a pink oil.

후처리

  1. customThe solvent was evaporated under vacuum
  2. washThe residue in EtOAc (150 mL) was washed with water (5×100 mL) and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum to an oil (2.29 g)
  6. dissolutionThe crude product was dissolved in CH2CL2 (5 mL)
  7. filtrationthe solution filtered through a pad of EM silica gel 60 (20 mL)
  8. washto elute the silica gel
  9. customThe CH2Cl2 filtrate was evaporated under vacuum

출처 및 근거

ORD 기록
ord-835f01ea929a484fbdde0611e5ce74b3
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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