Dimethyl Sulfoxide → HCID 63802010, compound

HRID 2387568Notes

Reaction equation

HRID 2387568 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1C=O.O.C[S:18]([CH3:20])=O>>[F:7][C:8]1[CH:9]=[CH:12][C:13]([S:18][C:20]2[CH:14]=[CH:15][CH:8]=[CH:9][C:12]=2[CH:1]=[O:4])=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 11430Potassium CarbonateHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 63802010HCID 63802010, compoundYield 64%

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-fluorophenylthiol (0.86 ml, 8.06 mmol) and K2CO3 (2.50 g, 18.12 mmol) in DMSO (5 ml) was added 2-fluorobenzaldehyde (1.00 g, 8.06 mmol) under N2 and the mixture heated at 100° C. for 3 hours. The reaction was cooled to room temperature and water (20 ml) added. This mixture was extracted with ethyl acetate, the combined organic extracts were washed with saturated brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid (1.20 g, 5.17 mmol, 64%) δH (300 MHz, 4-DMSO) 10.23 (1H, s, CHO), 7.98 (1H, dd, J 7.3 and 1.7 Hz, Ar), 7.63-7.49 (3H, m, Ar), 7.45-7.32 (3H, m, Ar) and 6.88 (1H, d, J=7.7 Hz, Ar).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThis mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1763c2236ee6482b8ffc17812469a2d4
Source dataset
uspto-grants-2012_09
Patent number
US08268878B2

Reaction notes

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