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

HRID 38983

Reaction equation

HRID 38983 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH: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(=O)(O)[O-].[Na+]>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][CH:12]1[CH2:14][O:13]1)=[O:23]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 212209825-Bromo-2-(oxiran-2-ylmethoxy)benzaldehyde

Product 1

HCID 212210275-Bromo-2-(oxiran-2-ylmethoxy)phenyl formate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-2-(oxiran-2-ylmethoxy)benzaldehyde (12.3 g, 47.7 mmol) in DCM (50 ml) was added m-CPBA (12.8 g, 57.2 mmol). The solution was heated at reflux for 3 h and 30 min and then brought to ambient temperature. Aqueous sodium bicarbonate (saturated) and DCM was added and the phases were separated. The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to dryness to give the crude title compound. Crude yield: 12.3 g. MS m/z (rel. intensity, 70 eV) 272 (M+, 7), 244 (50), 189 (95), 188 (bp), 57 (93).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h and 30 min
  3. custombrought to ambient temperature
  4. customthe phases were separated
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-767b3078aa2d471d93d3027cc3832986
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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