m-Chloroperbenzoic acid → 2-[(4-Fluorobenzene-1-sulfinyl)methyl]pyridine

HRID 2286224Notes

Reaction equation

HRID 2286224 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:5][CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:22]>C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:22])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 127602222-{[(4-Fluorophenyl)sulfanyl]methyl}pyridine--hydrogen chloride (1/1)

Product 1

HCID 127602312-[(4-Fluorobenzene-1-sulfinyl)methyl]pyridineYield 54.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred suspension of 2-(((4-fluorophenyl)thio)methyl)pyridine, hydrochloride (2 g) in methylene chloride (50 ml) at 0° C. was treated portionwise with m-chloroperoxybenzoic acid (1.8 g) over 1/2 hour. The mixture was allowed to warm to ambient temperature and the mixture was stirred for a further 4 hours. The solution was washed with saturated Na2CO3 solution and water, dried (MgSO4) and evaporated. The residue was recrystallised from diisopropyl ether to give the title compound (1.0 g) mp 92°-4° C. (Found: C,60.9; H,4.6; N,5.6 C12H10FNOS requires C,61.3; H,4.3; N,5.95%).

Workup

  1. washThe solution was washed with saturated Na2CO3 solution and water
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-3b8d0cd472f74e539478521f608ead7b
Source dataset
uspto-grants-1982_04
Patent number
US04327102

Reaction notes

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