m-Chloroperbenzoic acid → HCID 58463270, compound

HRID 1748947Notes

Reaction equation

HRID 1748947 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[S:7][CH3:8].ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[S:7]([CH3:8])=[O:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 134152162-Bromo-3-(methylsulfanyl)thiophene

Product 1

HCID 58463270HCID 58463270, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 25 (3.64 g, 17.4 mmol) in CH2Cl2 (100 mL) at −40° C., was added 3-chloroperbenzoic acid (3 g, 17.4 mmol) in CH2Cl2 (50 mL) dropwise and the resulting solution was allowed to stir at room temperature overnight. The reaction mixture was washed with aqueous Na2CO3, dried with anhydrous sodium sulfate and evaporated in vacuum. Column chromatography (silica gel, hexane/EtOAc (1/2) yields the pure compound 26 (2.74 g, 70%). 1H NMR (CDCl3): δ 2.82 (3H, s), 7.35 (1H, d), 7.43 (1H, d). MS (EI): calcd, 225.1. found M+, 210.1=product-16).

Workup

  1. washThe reaction mixture was washed with aqueous Na2CO3
  2. dry with materialdried with anhydrous sodium sulfate
  3. customevaporated in vacuum

Sources & evidence

ORD record
ord-0597d1d73c8540699fa3441ffb9c7ec4
Source dataset
uspto-grants-2015_10
Patent number
US09153785B2

Reaction notes

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