m-Chloroperbenzoic acid → HCID 59346894, compound

HRID 20536Notes

Reaction equation

HRID 20536 reaction equation
[CH3:1][CH2:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([Cl:11])[CH:5]=1.ClC1C=CC=C(C(OO)=[O:20])C=1>C(Cl)Cl>[Cl:11][C:6]1[CH:5]=[C:4]([S:3]([CH2:2][CH3:1])=[O:20])[CH:9]=[CH:8][C:7]=1[F:10]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 552207103-Chloro-4-fluorophenyl ethyl sulfide

Product 1

HCID 59346894HCID 59346894, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-4-ethanesulphanyl-1-fluorobenzene (2.40 g) in DCM (100 mL) was added 75% m-chloroperbenzoic acid (4.35 g) and the mixture stirred at ambient temperature for 16 h. The mixture was washed successively with saturated potassium carbonate (30 mL) and brine (30 mL) then dried (MgSO4), filtered and reduced in vacuo. The resultant residue was chromatographed on silica (eluting with 0-50% ethyl acetate in iso-hexane) and the slower running product isolated (1.26 g).

Workup

  1. washThe mixture was washed successively with saturated potassium carbonate (30 mL) and brine (30 mL)
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customThe resultant residue was chromatographed on silica (eluting with 0-50% ethyl acetate in iso-hexane)
  5. customisolated (1.26 g)

Sources & evidence

ORD record
ord-74bee4a2e00240e489f20dde262c87db
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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