Cesium carbonate → 1-Bromo-4-(2-chlorophenylsulfanyl)-benzene

HRID 1468336ノート

反応式

HRID 1468336 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]=[CH:14][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.[Cu]Cl.CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[Cl:9])=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 119931-Chloro-2-iodobenzeneHCID 660494-BromothiophenolHCID 11191887Heptanedione, tetramethyl-

生成物 1

HCID 197368221-Bromo-4-(2-chlorophenylsulfanyl)-benzene収率 55.6%

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. To this mixture was added 2-chloro-iodobenzene (0.63 g, 2.64 mmol). Copper(I) chloride (0.131 g, 1.32 mmol), tetramethyl heptanedione (0.14 mL, 0.66 mmol) and cesium carbonate (1.70 g, 5.22 mmol) were added. 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-bromo-4-(2-chlorophenylsulfanyl)-benzene (0.44 g). MS calcd. for C12H8BrS [(M−Cl)] 265, obsd. 265.

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-d202b246e3fd4eb3bcc166d630b4ca81
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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