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

HRID 39005Notes

Reaction equation

HRID 39005 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:16])[C:5]([O:11][CH2:12][C@H:13]2[CH2:15][O:14]2)=[C:6](CC=O)[CH:7]=1.C1C=C(Cl)C=[C:19]([C:24]([O:26]O)=[O:25])C=1>C(Cl)(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][C@H:13]1[CH2:15][O:14]1)(=[O:25])[CH3:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866529475-bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxyphenyl)ethanone

Product 1

HCID 866529465-Bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxy]phenyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Preparation according to Preparation 7 using 1-(5-bromo-3-fluoro-2-[(2R)-oxiran-2-ylmethoxyphenyl)ethanone (19.5 g, 67 mmol), CHCl3 and m-CPBA (77%, 60.5 g, 27 mmol). The mixture was heated at reflux for 24 h. The crude product was further used (Preparation 25). MS m/z (rel. intensity, 70 eV) 306 (M+, 4), 304 (M+, 4) 262 (bp), 69 (69), 57 (99).

Workup

  1. customPreparation
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 24 h
  4. custom(Preparation 25)

Sources & evidence

ORD record
ord-667f8a43232045bcba8934513a35705c
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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