Pyridiniumtribromide → 2-Bromo-1-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanone

HRID 30874노트

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HRID 30874 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:5]=[CH:6][C:7]=1[C:8](=[O:10])[CH3:9].[Br-:20].[Br-].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(O)(=O)C>[Br:20][CH2:9][C:8]([C:7]1[CH:6]=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:3][C:2]=1[CH3:1])=[O:10]

참가 물질

4

반응물 2

HCID 21124087PyridiniumtribromideHCID 219857981-(3-Methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanone

생성물 1

HCID 219856882-Bromo-1-(3-methyl-4'-nitro-1,1'-biphenyl-4-yl)ethanone수율 59%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
110 °C

실험 절차

A mixture of 1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone (5.66 g, 22 mmol), pyridinium tribromide (10.63 g, 33.0 mmol), and glacial acetic acid (60 mL) was stirred at 110° C. for 3 h. The reaction mixture was cooled to 0-5° C., and the precipitated product was collected by filtration and washed with small amounts of water, ethanol, and diethyl ether. The crude material was purified by flash chromatography (5:95 ethyl acetate/hexane) to give 2-bromo-1-(3-methyl-4′-nitro-1,1′-biphenyl-4-yl)ethanone as a light yellow solid (4.33 g, 59% yield). HPLC ret. time 3.63 min; 1H NMR (CDCl3) δ: 2.63 (s, 3H), 2.25 (s, 2H), 7.52-7.58 (m, 2H), 7.72-7.83 (m, 3H), 8.32 (d, 2H).

후처리

  1. temperatureThe reaction mixture was cooled to 0-5° C.
  2. filtrationthe precipitated product was collected by filtration
  3. washwashed with small amounts of water, ethanol, and diethyl ether
  4. customThe crude material was purified by flash chromatography (5:95 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-13f279f0c2114ca1b1c429ba8eb11603
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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