Potassium Carbonate → HCID 86614984, compound

HRID 2378568Notes

Reaction equation

HRID 2378568 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH:17]1([SH:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:22][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15510CyclopentanethiolHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 86614984HCID 86614984, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 3-bromo-4-fluorobenzaldehyde (517.4 mg) in DMSO (8 ml) was added with potassium carbonate (514.9 mg) and cyclopentanethiol (250 μl, TCI), and stirred at 90° C. for 17 hours. The reaction mixture was extracted with ethyl acetate (50 ml), and the organic layer was washed successively with water and saturated brine, and dried. Then, the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=8:1) to obtain the title compound (Intermediate S-23, 644.7 mg).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (50 ml)
  2. washthe organic layer was washed successively with water and saturated brine
  3. customdried
  4. customThen, the solvent was evaporated under reduced pressure
  5. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-1f4bfc4ec7ed452ea817993401182c4a
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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