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

HRID 33571ノート

反応式

HRID 33571 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 2311612-Bromo-1'-propionaphthone収率 118.2%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-17bbc17884dc4eae925ca8fc9dd03b88
出典データセット
uspto-grants-2008_09
特許番号
US07429607B2

反応ノート

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