m-Chloroperbenzoic acid → Methyl 3-bromo-5-(oxiran-2-yl)benzoate

HRID 1845333Notes

Reaction equation

HRID 1845333 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]=[CH2:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].ClC1C=CC=C(C(OO)=[O:22])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:12]2[CH2:13][O:22]2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58188041Methyl 3-bromo-5-vinylbenzoate

Product 1

HCID 58188045Methyl 3-bromo-5-(oxiran-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 3-bromo-5-vinylbenzoate (1.00 g, 4.15 mmol) in CH2Cl2 (40 mL) at 0° C. was added m-chloroperbenzoic acid (70% purity, 1.43 g, 5.80 mmol) in portions over a 10 minute period. The mixture was warmed to room temperature and stirred for 2 hours upon which it was poured onto saturated sodium bicarbonate (250 mL). The mixture was extracted with ethyl acetate (3×100 mL) and the combined extracts were dried over Na2SO4 and concentrated. The residue was purified by column chromatography (0-50% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): 7.92 (t, 1H, J=1.7 Hz), 7.86 (t, 1H, J=1.5 Hz), 7.78 (t, 1H, J=1.7 Hz), 4.09 (q, 1H, J=2.5 Hz), 3.87 (s, 3H), 3.17-3.14 (m, 1H), 2.92-2.90 (m, 1H).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. dry with materialthe combined extracts were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (0-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-430feb4064214fb788b7411cda03eefa
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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