m-Chloroperbenzoic acid → (4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxide

HRID 325535Notes

Reaction equation

HRID 325535 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([S:18][CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([CH3:35])[CH:29]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([S:18]([CH2:19][C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[C:30]([CH3:35])[CH:29]=2)=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13316982(4'-Fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-YL)methyl phenyl sulfide

Product 1

HCID 13316983(4'-Fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl)phenyl sulfoxide

Conditions

Temperature
-78 °C

Procedure

m-Chloroperbenzoic acid (tech. grade, approximately 75% peroxide; 1.19 g, aproximately 5 mmoles) was added in small portions to a stirred solution of (4'-fluoro-3,3',5-trimethyl-[1,1'-biphenyl]-2-yl-methyl) phenyl sulfide (1.68 g, 5 mmoles) at -78° C. The reaction mixture was then stirred at -78° C. for 30 minutes and allowed to warm to room temperature. The solution of the product was separated by filtration from the 3-chlorobenzoic acid which was washed with methylene chloride. The combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml then washed with dilute sodium hydroxide solution (2×50 ml) dried (MgSO4), filtered, and the solvent was evaporated in vacuo to leave 1.7 g of crude product. This was purified by flash chromatography on silica gel using a 40×150 mm column eluting with 3.5% (v:v) acetone in methylene chloride to give 1.55 g of the title compound as a gum. Dry toluene was added and evaporated in vacuo four times to dry the product, which then crystallized, m.p. 75°-85° C. Calc'd for C22H21FSO: C, 74.97; H, 6.01 Found: C, 75.01, H, 6.19.

Workup

  1. temperatureto warm to room temperature
  2. customThe solution of the product was separated by filtration from the 3-chlorobenzoic acid which
  3. washwas washed with methylene chloride
  4. additionThe combined methylene chloride solutions of the product were diluted with methylene chloride to 100 ml
  5. washthen washed with dilute sodium hydroxide solution (2×50 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuo
  9. customto leave 1.7 g of crude product
  10. customThis was purified by flash chromatography on silica gel using a 40×150 mm column
  11. washeluting with 3.5% (v:v) acetone in methylene chloride

Sources & evidence

ORD record
ord-2d6e0da4373749fe8e3e863f5aa9d794
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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