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

HRID 1713304
Notes
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Reaction equation

HRID 1713304 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2f3b94bd8dbd46598a4d2b33490d6713
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07795236B2

Reaction notes

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