Potassium Carbonate → 1-Bromomethylsulfinyl-4-chlorobenzene

HRID 1982547Notes

Reaction equation

HRID 1982547 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([S:14]([CH2:13][Br:12])=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 135300861-Bromomethylthio-4-chlorobenzene

Product 1

HCID 156504781-Bromomethylsulfinyl-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

90% m-Chloroperbenzoic acid (17 mmol) in chloroform (35 ml) solution was added dropwise with stirring over 1 h at 0° C. to a solution of 1-bromomethylsulfenyl-4-chlorobenzene (15 mmol) in chloroform (35 ml). The mixture was stirred at room temperature overnight, shaken with 1M K2CO3 aq., the dried (MgSO4) chloroform solution evaporated and the solid residue recrystallized from CHCl3 : pet. ether; yield 3.20 g (84%), m.p. 100° C. 1H NMR (CDCl3): δ 4.28 (CH2), 7.53 (Ph). IR (KBr): 1040-1030 cm-1 (SO).

Workup

  1. dry with materialthe dried (MgSO4) chloroform solution
  2. customevaporated
  3. customthe solid residue recrystallized from CHCl3

Sources & evidence

ORD record
ord-53d63ba996144a57bfa61effaba6df51
Source dataset
uspto-grants-1986_06
Patent number
US04596870

Reaction notes

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