m-Chloroperbenzoic acid → 5-Bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate

HRID 38988Notes

Reaction equation

HRID 38988 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C@@H:12]2[CH2:14][O:13]2)=[C:6]([CH:9]=1)C=O.C1C=C(Cl)C=C([C:22]([O:24]O)=[O:23])C=1>C(Cl)Cl>[CH:22]([O:24][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C@@H:12]1[CH2:14][O:13]1)=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866529415-Bromo-2-[(2S)-oxiran-2-ylmethoxy]benzaldehyde

Product 1

HCID 866529425-Bromo-2-[(2S)-oxiran-2-ylmethoxy]phenyl formate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 2 using 5-bromo-2-[(2S)-oxiran-2-ylmethoxy]benzaldehyde (8.3 g, 32 mmol), DCM (100 ml) and m-CPBA (77%, 10.9 g, 48.6 mmol). The mixture was heated at reflux for 3 h. Crude yield: 8.5 g. MS m/z (rel. intensity, 70 eV) 274 (M+, 10), 273 (M+, 9), 189 (98), 188 (bp), 57 (77).

Workup

  1. customPreparation
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-5638e0f88eee40a39b01485c97fcf353
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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