4-Fluorobenzenesulfonyl chloride → HCID 66924788, compound

HRID 554178Notes

Reaction equation

HRID 554178 reaction equation
FC1C=CC(C(=O)CBr)=CC=1.[C:12]([CH:14]([CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].FC1C=CC(C2NC=C(C(OCC)=O)C=2)=CC=1.[H-].[Na+].[F:49][C:50]1[CH:55]=[CH:54][C:53]([S:56](Cl)(=[O:58])=[O:57])=[CH:52][CH:51]=1>CN(C)C=O.O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[N:13]([S:56]([C:53]3[CH:54]=[CH:55][C:50]([F:49])=[CH:51][CH:52]=3)(=[O:58])=[O:57])[CH:12]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:20]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 19979312HCID 19979312, compoundHCID 66924929HCID 66924929, compound2×

Product 1

HCID 66924788HCID 66924788, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Using 4-fluorophenacyl bromide instead of phenacyl bromide, a procedure as in Reference Example 1 was performed to synthesize ethyl 2-cyano-4-(4-fluorophenyl)-4-oxobutanoate, and procedures as in Reference Examples 2 and 3 were performed to synthesize ethyl 5-(4-fluorophenyl)-1H-pyrrole-3-carboxylate. Sodium hydride (60% in oil, 0.58 g) was added to a solution (20 mL) of ethyl 5-(4-fluorophenyl)-1H-pyrrole-3-carboxylate (2.85 g) in N,N-dimethylformamide under ice-cooling. The mixture was stirred at the same temperature for 15 min, 4-fluorobenzenesulfonyl chloride (2.92 g) was added, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as crystals (yield 4.66 g, 97%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b3b0ea12a91e44dd9b50d153daa3c026
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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