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Potassium Carbonate → 3-(3-Bromophenylsulfanyl)propane-1-ol

HRID 1713304
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HRID 1713304 반응식
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].C([O:18][CH2:19][CH2:20][CH2:21]Cl)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:21][CH2:20][CH2:19][OH:18])[CH:5]=[CH:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 123341-Propanol, 3-chloro-, acetateHCID 80597m-Bromobenzenethiol

생성물 1

HCID 585220973-(3-Bromophenylsulfanyl)propane-1-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

3-Bromobenzenethiol (0.40 g) and potassium carbonate (0.44 g) were suspended in N,N-dimethylformamide (4.2 mL), 3-chloropropyl acetate (0.34 mL) was added, and the resulting mixture was stirred at 60° C. for 5 hours. The reaction mixture was partitioned between diethyl ether (40 mL) and water (10 mL). The organic layer was washed successively with water (10 mL×2) and brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in methanol (8.5 mL), 28% sodium methoxide-methanol solution (0.08 mL) was added, and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to give the title compound (0.49 g).

후처리

  1. customThe reaction mixture was partitioned between diethyl ether (40 mL) and water (10 mL)
  2. washThe organic layer was washed successively with water (10 mL×2) and brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (8.5 mL)
  6. addition28% sodium methoxide-methanol solution (0.08 mL) was added
  7. stirringthe resulting mixture was stirred at room temperature for 2 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. customthe residue obtained
  10. customwas purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-2f3b94bd8dbd46598a4d2b33490d6713
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07795236B2

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