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

HRID 38993Notes

Reaction equation

HRID 38993 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 541570455-Bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehyde

Product 1

HCID 541488055-Bromo-2-[(2R)-oxiran-2-ylmethoxy]phenyl formate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 2 using 5-bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehyde (6.8 g, 26 mmol), DCM (75 ml) and m-CPBA (77%, 8.9 g, 39.5 mmol). Crude yield: 7.0 g. MS m/z (rel. intensity, 70 eV) 274 (M+, 10), 273 (M+, 9), 189 (98), 188 (bp), 57 (77).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-41fa640187ef4f8fb80b08c6f01dcd71
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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