Cesium carbonate → 1-(4-Bromo-phenylsulfanyl)-2,4-dichlorobenzene

HRID 1468342ノート

反応式

HRID 1468342 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1I.CC(CCC)C(=O)C(=O)C(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.Cl[Cu].CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:15][C:14]=2[Cl:16])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 660494-BromothiophenolHCID 968642,4-Dichloro-1-iodobenzeneHCID 11191887Heptanedione, tetramethyl-

生成物 1

HCID 866949361-(4-Bromo-phenylsulfanyl)-2,4-dichlorobenzene収率 79.4%

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
130 °C

実験手順

N-Methyl-2-pyrrolidone (10 mL) was added to 4-bromothiophenol (0.500 g, 2.64 mmol) in a sealed tube and the mixture was purged with argon for 5 minutes. After this time, 2,4-dichloroiodobenzene (0.72 g, 2.64 mmol), CuCl (0.131 g, 1.32 mmol), tetramethyl heptanedione (0.14 mL, 0.66 mmol) and cesium carbonate (1.70 g, 5.28 mmol) were added to the reaction mixture. The reaction mixture was stirred at 130° C. under argon for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and filtered through a celite bed. The filtrate was washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield the crude product. Silica gel chromatography (neat hexanes) provided impure 1-(4-bromo-phenylsulfanyl)-2,4-dichloro-benzene (0.7 g).

後処理

  1. customthe mixture was purged with argon for 5 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through a celite bed
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto yield the crude product

出典と根拠

ORDレコード
ord-221757058c90438caa18dee05848cb74
出典データセット
uspto-grants-2015_04
特許番号
US09000044B2

反応ノート

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