m-Chloroperbenzoic acid → 5-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetate

HRID 39025Notes

Reaction equation

HRID 39025 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:16])[C:5]([O:11][CH2:12][CH:13]2[CH2:15][O:14]2)=[C:6](C(=O)C)[CH:7]=1.C1C=C(Cl)C=[C:19]([C:24]([O:26]O)=[O:25])C=1>C(Cl)Cl>[C:24]([O:26][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([Cl:16])[C:5]=1[O:11][CH2:12][CH:13]1[CH2:15][O:14]1)(=[O:25])[CH3:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 866529521-[5-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl]ethanone

Product 1

HCID 866529535-Bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl acetateYield 149.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 1-[5-bromo-3-chloro-2-(oxiran-2-ylmethoxy)phenyl]ethanone (1.7 g, 5.6 mmol) and m-CPBA (2.4 g, 14 mmol) in DCM (30 ml) was heated to 50° C. After 22 h more m-CPBA (2.4 g, 14 mmol) was added and the mixture was heated at 50° C. for another 44 h and then brought to ambient temperature. The solid was filtered off and rinsed. The resulting filtrate was washed with sodium bicarbonate (saturated), brine and further dried (Na2SO4) and evaporated to dryness to give the crude title compound (2.7 g). MS m/z (rel. intensity, 70 eV) 280 (bp), 278 (84), 224 (54), 222 (52), 57 (79), 322 (M+, 5).

Workup

  1. custombrought to ambient temperature
  2. filtrationThe solid was filtered off
  3. washrinsed
  4. washThe resulting filtrate was washed with sodium bicarbonate (saturated), brine
  5. dry with materialfurther dried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-38de70a30356476493ede3110e26fb5d
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

Loading…