Water → HCID 17901415, compound

HRID 1936545Notes

Reaction equation

HRID 1936545 reaction equation
CS(O[C:6]#[C:7][CH3:8])(=O)=O.[Br:9][C:10]1[C:11]([C:21]2[CH:26]=[C:25]([OH:27])[C:24]([Cl:28])=[CH:23][C:22]=2[F:29])=[C:12]([Cl:20])[N:13]([CH3:19])[C:14]=1[C:15]([F:18])([F:17])[F:16].C(=O)([O-])[O-].[K+].[K+].O>CC(CC(C)C)=O>[Br:9][C:10]1[C:11]([C:21]2[CH:26]=[C:25]([O:27][CH2:8][C:7]#[CH:6])[C:24]([Cl:28])=[CH:23][C:22]=2[F:29])=[C:12]([Cl:20])[N:13]([CH3:19])[C:14]=1[C:15]([F:16])([F:17])[F:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 13720434HCID 13720434, compoundHCID 22462101HCID 22462101, compound

Product 1

HCID 17901415HCID 17901415, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

2 propinyl methanesulfonate (0.22 g; 1.61 mmoles) is added to a mixture of 4-bromo-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-chloro-1-methyl-5-trifluoromethyl pyrrole (0.6 g; 1.47 mmoles) and potassium carbonate (0.21 g; 1.54 mmoles) in methylisobutylketone (6 ml). The mixture is heated to 80° C. for 3 hours. The reaction mixture is poured into water (10 ml), extracted with ethyl ether (3×20 ml), the ether phase is washed with a saturated solution of sodium chloride, anhydrified with sodium sulfate and concentrated in a rotavapor. The raw product obtained (0.65 g) is chromatographed on silica gel, eluating with n-hexane/ethyl acetate 85:15. 0.28 g of solid white product with a melting point of 87° C., are obtained.

Workup

  1. extractionextracted with ethyl ether (3×20 ml)
  2. washthe ether phase is washed with a saturated solution of sodium chloride
  3. concentrationconcentrated in a rotavapor
  4. customThe raw product obtained (0.65 g)
  5. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-30b3db7ba5bd4ca0884208643e91e57d
Source dataset
uspto-grants-2002_05
Patent number
US06391827B1

Reaction notes

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