Potassium Carbonate → HCID 12016882, compound

HRID 1936206Notes

Reaction equation

HRID 1936206 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[C:23]([SH:24])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].ClC1C=CC=C(C(OO)=[O:37])C=1.[OH-:40].[Na+]>CN(C=O)C.ClCCl>[F:17][C:18]1[C:23]([S:24]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:37])=[O:40])=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 13042Benzenethiol, pentafluoro-HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 1650214-Methoxybenzyl bromide

Product 1

HCID 12016882HCID 12016882, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzylbromide (2.00 g, 9.95 mmol) in DMF (20 ml) at room temperature was added potassium carbonate (2.07 g, 15.0 mmol) followed by pentafluorothiophenol (1.33 ml, 9.97 mmol). After stirring at room temperature for 1 h, the reaction mixture was poured onto water and extracted with diethyl ether. The combined organic extracts were washed with 1 M NaOH, dried and concentrated to give a white solid which was used directly in the next step. The sulfide (1.11 g, 3.47 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. m-chloroperbenzoic acid, MCPBA, (1.20 g, 6.95 mmol) was added and the resulting mixture stirred at room temperature for 2 h The reaction mixture was poured onto 1 M NaOH (50 ml) and extracted with dichloromethane (3×25 ml). The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate) to provide 413 mg (34%) of the title compound as a white solid. 1H NMR (CDCl3): d 7.18-7.22 (2H, m), 6.85-6.80 (2H, m), 4.48 (2H, s), 3.78 (3H, s). MS (EI): m/z 352 (2, M+), 121 (100). Anal. Calcd for C14H9F5O3S: C, 47.73; H, 2.58; S, 9.10. Found: C, 47.88; H, 2.66; S, 8.97.

Workup

  1. additionthe reaction mixture was poured onto water
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed with 1 M NaOH
  4. customdried
  5. concentrationconcentrated
  6. customto give a white solid which
  7. additionwas added
  8. stirringthe resulting mixture stirred at room temperature for 2 h The reaction mixture
  9. extractionextracted with dichloromethane (3×25 ml)
  10. washThe combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash
  11. customchromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate)

Sources & evidence

ORD record
ord-f9198edad5664988a902245be04ae042
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

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