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

HRID 1057010ノート

反応式

HRID 1057010 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d8231d3e86734e1ba0f561fc87a9402c
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

読み込み中…