1-Naphthalen-1-ylpropan-1-one → 2-Bromo-1'-propionaphthone

HRID 33571노트

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HRID 33571 반응식
[C:1]1([C:11](=[O:14])[CH2:12][CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br-:15].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>COCCOC>[Br:15][CH:12]([CH3:13])[C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:14]

참가 물질

4

반응물 2

HCID 2311591-Naphthalen-1-ylpropan-1-oneHCID 17977687Phenyltrimethylammonium bromide dibromide

생성물 1

HCID 2311612-Bromo-1'-propionaphthone수율 118.2%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

To a solution of 1-naphthalen-1-yl-propan-l-one (37.8 g) in 1,2-dimethoxyethane (350 mL) at 0° C. was added phenyl trimethylammonium tribromide (83 g). The mixture was stirred at 0° C. for 10 minutes and then at room temperature for 24 hours. The mixture was washed with water (500 mL) and the aqueous phase was extracted with ethyl acetate (2×500 mL). The combined organics were washed with water (2×200 mL), brine (500 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford an orange gum. The gum was triturated with diethyl ether and filtered to afford 2-bromo-1-naphthalen-1-yl-propan-1-one (39.8 g, 74%) as an orange solid, 1H NMR (CDCl3): 1.95 (3H, d, J=6.6 Hz), 5.35 (1H, q, J=6.6 Hz), 7.45-7.60 (3H, m), 7.85-7.90 (2H, m), 8.0 (1H, d, J=8.1 Hz), 8.4 (1H, d, J=7.9 Hz).

후처리

  1. waitat room temperature for 24 hours
  2. washThe mixture was washed with water (500 mL)
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×500 mL)
  4. washThe combined organics were washed with water (2×200 mL), brine (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto afford an orange gum
  9. customThe gum was triturated with diethyl ether
  10. filtrationfiltered

출처 및 근거

ORD 기록
ord-17bbc17884dc4eae925ca8fc9dd03b88
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429607B2

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