m-Chloroperbenzoic acid → HCID 59750791, compound

HRID 748664Notes

Reaction equation

HRID 748664 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH:21]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[CH2:22][CH2:23][CH2:24][CH3:25])=[O:20])=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([CH:21]([C:26]2[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=2[F:33])[CH2:22][CH2:23][CH2:24][CH3:25])(=[O:9])=[O:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59750911HCID 59750911, compound

Product 1

HCID 59750791HCID 59750791, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

After addition of 3-chloroperbenzoic acid (98.8 mg, 0.571 mmol) to a solution of 2-[1-[(4-chlorophenyl)sulfinyl]pentyl]-1,4-difluorobenzene (Isomer 2-B) (150 mg, 0.439 mmol) in methylene chloride (5 ml), the resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with methylene chloride, washed successively with a 1N aqueous solution of sodium hydroxide, water and brine, dried over MgSO4, and concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane), whereby the title compound (122 mg, 77%) was obtained as a colorless oil.

Workup

  1. washwashed successively with a 1N aqueous solution of sodium hydroxide, water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. customwas purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane), whereby the title compound (122 mg, 77%)
  6. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-b3c00803f5c2461fa564ec518f62c6cc
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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