Sodium Sulfite → 1-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]benzene

HRID 1839921Notes

Reaction equation

HRID 1839921 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Cl[C:23]1C=C(C=CC=1)C(OO)=O.[O-:33][S:34]([O-:36])=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([S:34]([CH3:23])(=[O:36])=[O:33])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 23450971HCID 23450971, compound

Product 1

HCID 99054121-(4-Fluorophenyl)-2-[4-(methylsulfonyl)phenyl]benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 550 mg (1.9 mmol) of crude 1-(4-fluoro-phenyl)-2-[4-(methylthio)phenyl]benzene (Step 3) in 10 mL of methylene chloride at ambient temperature was slowly added 1.3 g (4.1 mmol) of 3-chloroperoxybenzoic acid (ca. 55%). Stirring was continued for 20 minutes prior to the addition of 1 g of Na2SO3. The reaction was allowed to stir for an additional 10 minutes and the solvent removed in vacuo. The residue was dissolved in ethyl acetate and the resulting solution washed twice with saturated NaHCO3 and dried over MgSO4. Recrystallization from ethyl acetate/hexane gave 437 mg (94%) of 1-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 178.0-179.0° C.; NMR (CDCl3) δ 3.05 (s, 3H), 6.93 (t, J=8 Hz, 2H), 7.03-7.09 (m, 2H), 7.32 (d, J=8 Hz, 2H), 7.38-7.50 (m, 4H), 7.80 (d, J=8 Hz, 2H). MS (FAB): m/e 333 (M+Li). Anal. Calc'd for C19 H15FO2S: C, 69.86; H, 4.60; F, 5.79. Found: c, 69.74; H, 4.72; F, 5.51.

Workup

  1. customat ambient temperature
  2. stirringto stir for an additional 10 minutes
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe resulting solution washed twice with saturated NaHCO3
  6. dry with materialdried over MgSO4
  7. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-dcf8d15a31494286817baae20cc52571
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

Loading…