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

HRID 1468342노트

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HRID 1468342 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 62652Cuprous chloride촉매HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-221757058c90438caa18dee05848cb74
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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