Thiophenol → Methyl 4-(phenylsulfanylmethyl)benzoate

HRID 1727265Notes

Reaction equation

HRID 1727265 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23]Br)=[CH:19][CH:18]=1>CN(C=O)C>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 366566Methyl 4-(phenylsulfanylmethyl)benzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of benzenethiol (1.3 mL, 13.1 mmol) and potassium tert-butoxide (1.47 g, 13.1 mmol) in DMF (50 mL) at 0° C. was added 4-(bromomethyl)benzoic acid methyl ester (3.0 g, 13.1 mmol), and the mixture was stirred at room temperature for 1 hour. After stirring at 80-90° C. overnight, the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water (30 mL) and extracted with CH2Cl2 (200 mL). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by MPLC on silica gel (10% EtOAc in hexanes) to afford the titled compound (2.74 g, 81%) as a white solid.

Workup

  1. stirringAfter stirring at 80-90° C. overnight
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in water (30 mL)
  4. extractionextracted with CH2Cl2 (200 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by MPLC on silica gel (10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-202461df03124465a16b3108c758693b
Source dataset
uspto-grants-2009_02
Patent number
US07495022B2

Reaction notes

Loading…