m-Chloroperbenzoic acid → HCID 22147654, compound

HRID 1884835Notes

Reaction equation

HRID 1884835 reaction equation
[F:1][CH:2]([F:18])[S:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)=[O:4].C1C=C(Cl)C=C(C(OO)=[O:27])C=1>C(Cl)Cl>[F:18][CH:2]([F:1])[S:3]([C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([F:16])=[CH:11][CH:12]=2)[N:7]([CH3:17])[CH:6]=1)(=[O:27])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 10446064HCID 10446064, compound

Product 1

HCID 22147654HCID 22147654, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-difluoromethylsulfinyl-7-fluoro-1-methyl-4-quinolone (5) (79 mg, 0.287 mmol) in DCM (8 mL) was added ˜80% MCPBA (55.7 mg, 0.258 mmol). The mixture was stirred at a room temperature overnight. An additional amount of MCPBA (15 mg) was added and stirring was continued for 3 days. The mixture was diluted with DCM (10 mL), washed with 5% aqueous Na2CO3 (3×5 mL), the aqueous layers were extracted with DCM (2×10 mL), the combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue, e.g., the crude product, was recrystallized from ethyl acetate to give 27 mg (32%) of white crystals [3-difluoromethyl sulfonyl-7-fluoro-1-methyl-4-quinolone (6)]. The filtrate was chromatographed on silica gel with ethyl acetate-hexane (gradient 1:2, 1:1) to give second crop of the product [3-difluoromethylsulfonyl-7-fluoro-1-methyl-4-quinolone (6)] (32 mg, 38%) for a total yield 70%. This 3-difluoromethylsulfonyl-7-fluoro-1-methyl-4-quinolone gave the following NMR profile:

Workup

  1. stirringstirring
  2. waitwas continued for 3 days
  3. washwashed with 5% aqueous Na2CO3 (3×5 mL)
  4. extractionthe aqueous layers were extracted with DCM (2×10 mL)
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue, e.g., the crude product, was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-47242b21dcb542d6aa27c2503b715073
Source dataset
uspto-grants-2004_07
Patent number
US06767914B2

Reaction notes

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