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

HRID 2403692ノート

反応式

HRID 2403692 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 445513181-Bromo-2-methoxy-4-methyl-5-nitrobenzene収率 88.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 24477Sodium Thiosulfate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3689605b9f9f4e8c97d139037ca6da87
出典データセット
uspto-grants-2014_08
特許番号
US08802688B2

反応ノート

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