Cesium carbonate → HCID 86694942, 화합물

HRID 1468348

반응식

HRID 1468348 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[F:9][C:10]1[CH:11]=[C:12](I)[CH:13]=[C:14]([F:16])[CH:15]=1.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:12]2[CH:11]=[C:10]([F:9])[CH:15]=[C:14]([F:16])[CH:13]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 660494-BromothiophenolHCID 27782211,3-Difluoro-5-iodobenzeneHCID 11191887Heptanedione, tetramethyl-

생성물 1

HCID 86694942HCID 86694942, 화합물수율 78.2%

시약·촉매·용매 3

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

반응 조건

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, 3,5-difluoroiodobenzene (0.63 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)-3,5-difluorobenzene (0.622 g). MS calcd. for C12H8BrF2S [(M+H)+] 302, obsd. 302.

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-7c4dda7f90cf43afa3c05578424fa0a5
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000044B2

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