m-Chloroperbenzoic acid → Methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]sulfonyl}benzoate

HRID 735333Notes

Reaction equation

HRID 735333 reaction equation
ClC1C=C(C=CC=1)C(OO)=O.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([S:29][C:30]4[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=4[C:32]([O:34][CH3:35])=[O:33])[CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1.[OH-:40].[Ca+2].[OH-:42]>ClCCl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([S:29]([C:30]4[CH:39]=[CH:38][CH:37]=[CH:36][C:31]=4[C:32]([O:34][CH3:35])=[O:33])(=[O:42])=[O:40])[CH:25]=3)[N:20]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 68901056Methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]thio}benzoate

Product 1

HCID 68900676Methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]sulfonyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (77%; 597 mg, 2.67 mmol) was added to a solution of methyl 2-{[2-(4-fluorophenyl)quinolin-6-yl]thio}benzoate (346 mg, 0.89 mmol) in dichloromethane (15 mL). The resulting mixture was stirred at room temperature under nitrogen for 1 hour 20 minutes. Calcium hydroxide (308 mg, 4.16 mmol) was added and the resulting slurry stirred for 1 hour 15 minutes. The mixture was filtered and the filter cake washed thoroughly with dichloromethane. The filtrate was evaporated and the residue given a preliminary purification by elution from a silica pad with dichloromethane then 2.5% ethyl acetate/dichloromethane to afford an oil. Crystallisation from diethyl ether gave the title compound, in two crops, as pale yellow crystals (301 mg, 80%). 1H NMR (500 MHz, CDCl3) δ 8.57 (1H, d, J 1.7 Hz), 8.36 (1H, d, J 8.7 Hz), 8.25-8.15 (5H, m), 7.95 (1H, d, J 8.6 Hz), 7.67-7.65 (2H, m), 7.61 (1H, m), 7.22 (2H, t, J 8.6 Hz), 3.95 (3H, s); m/z (ES+) 422 [MH+].

Workup

  1. stirringthe resulting slurry stirred for 1 hour 15 minutes
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed thoroughly with dichloromethane
  4. customThe filtrate was evaporated
  5. customa preliminary purification
  6. washby elution from a silica pad with dichloromethane
  7. custom2.5% ethyl acetate/dichloromethane to afford an oil
  8. customCrystallisation from diethyl ether

Sources & evidence

ORD record
ord-d7083a001d284983a5ea324014a38c1a
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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