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

HRID 1713304
ノート
印刷プレビュー

反応式

HRID 1713304 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2f3b94bd8dbd46598a4d2b33490d6713
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795236B2

反応ノート

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