m-Chloroperbenzoic acid → HCID 86683468, compound

HRID 515804Notes

Reaction equation

HRID 515804 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]([F:27])([C:23]([F:26])([F:25])[F:24])[CH2:14][CH2:15][CH2:16][S:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22]>C(Cl)Cl>[F:27][C:13]([F:12])([C:23]([F:24])([F:25])[F:26])[CH2:14][CH2:15][CH2:16][S:17]([CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[O:9]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86683466HCID 86683466, compound

Product 1

HCID 86683468HCID 86683468, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

m-CPBA (64 mg, 0.37 mmol) was added to a cooled (0° C.) solution of 4-((4,4,5,5,5-pentafluoropentyl)thio)butan-1-ol (76 mg, 0.28 mmol) in DCM (3 mL) and it was stirred at 0° C. for 30 min. The reaction mixture was warmed to room temperature and was partitioned between a saturated solution of sodium bicarbonate and DCM. The organic layer was dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0 to 10% MeOH/DCM to afford 52 mg of 4-((4,4,5,5,5-pentafluoropentyl)sulfinyl)butan-1-ol as a white solid.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customwas partitioned between a saturated solution of sodium bicarbonate and DCM
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography on silica gel eluting with 0 to 10% MeOH/DCM

Sources & evidence

ORD record
ord-f882ac8c79b546b0ae34c515fe192ac2
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

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