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

HRID 39000Notes

Reaction equation

HRID 39000 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F: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]([F: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 866529431-[5-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone

Product 1

HCID 866529445-Bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl acetateYield 189.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[5-bromo-3-fluoro-2-(oxiran-2-ylmethoxy)phenyl]ethanone (1.3 g, 4.5 mmol) and m-CPBA (4.0 g, 18 mmol) in DCM (25 ml) was heated at reflux. After 22 h more m-CPBA (2.7 g, 12 mmol) was added and the mixture was heated at reflux for another 22 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 (2.6 g). MS m/z (rel. intensity, 70 eV) 305 (M+, 5), 304 (M+, 6), 263 (97), 262 (bp), 206 (49), 57 (65).

Workup

  1. temperatureat reflux
  2. temperaturethe mixture was heated
  3. temperatureat reflux for another 22 h
  4. custombrought to ambient temperature
  5. filtrationThe solid was filtered off
  6. washrinsed
  7. washThe resulting filtrate was washed with sodium bicarbonate (saturated), brine
  8. dry with materialfurther dried (Na2SO4)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-dbc3b18dcb914fe7bf3e099e362727d2
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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