Thiophenol → 4-Bromo-N-methyl-2-nitro-3-(phenylthio)aniline

HRID 1057010노트

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HRID 1057010 반응식
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1F.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O.C(OCC)(=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[S:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

7

반응물 3

HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 1180938324-Bromo-3-fluoro-N-methyl-2-nitroaniline

생성물 1

HCID 1180938504-Bromo-N-methyl-2-nitro-3-(phenylthio)aniline수율 97.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A solution of 4-bromo-3-fluoro-N-methyl-2-nitroaniline (0.30 g, 1.20 mmol) in N,N-dimethylformamide (2.45 mL) was treated with cesium carbonate (0.472 g, 1.45 mmol) and benzenethiol (0.149 mL, 1.45 mmol). The resultant reaction mixture was warmed to 80° C. and stirred at 80° C. for 30 min, after which time the reaction mixture was diluted with ethyl acetate and water. Layers were separated and the organic layer was washed with 10% solution of K2CO3 and brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the crude product. Purification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes) gave the desired product (396 mg, 97%) as an orange solid. LCMS calculated for C13H12BrN2O2S (M+H)+: m/z=339.0, 341.0. found: 338.9, 340.9.

후처리

  1. customThe resultant reaction mixture
  2. customLayers were separated
  3. washthe organic layer was washed with 10% solution of K2CO3 and brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customPurification by flash column chromatography (100% hexanes to 40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-d8231d3e86734e1ba0f561fc87a9402c
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

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