N-bromobutanimide → 1-Bromo-2-methoxy-4-methyl-5-nitrobenzene

HRID 2403692노트

반응식

HRID 2403692 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([CH3:12])[CH:4]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:13][C:8]1[CH:7]=[C:6]([N+:9]([O-:11])=[O:10])[C:5]([CH3:12])=[CH:4][C:3]=1[O:2][CH3:1]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 793303-Methyl-4-nitroanisole

생성물 1

HCID 445513181-Bromo-2-methoxy-4-methyl-5-nitrobenzene수율 88.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 24477Sodium Thiosulfate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 4-methoxy-2-methyl-1-nitrobenzene (2.0 g, 12 mmol) in N,N-dimethylformamide (5 mL) was added N-bromosuccinimide (8.52 g, 47.9 mmol). The reaction was heated to 100° C. for 1.5 hours. The reaction was cooled to room temperature and diluted with saturated aqueous sodium thiosulfate. The mixture was extracted with ethyl acetate (3×). The combined organics were washed with water, saturated sodium thiosulfate, and brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified via flash column chromatography (0-30% ethyl aceate/heptanes) to provide the title compound (2.6 g, ˜43% pure) as a pale yellow solid. 1H NMR (400 MHz, CDCl3, δ): 8.32 (s, 1 H), 6.74 (s, 1 H), 3.97 (s, 3 H), 2.63 (s, 3 H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organics were washed with water, saturated sodium thiosulfate, and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via flash column chromatography (0-30% ethyl aceate/heptanes)

출처 및 근거

ORD 기록
ord-3689605b9f9f4e8c97d139037ca6da87
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802688B2

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