m-Chloroperbenzoic acid → Racemic trans-3-(3-bromophenyl)oxiranemethanol

HRID 1275388Notes

Reaction equation

HRID 1275388 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15](/[CH:19]=[CH:20]/[CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=1>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C@@H:19]2[O:9][C@H:20]2[CH2:21][OH:22])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 186764783-(3-Bromophenyl)-2-propen-1-ol

Product 1

HCID 18665091Racemic trans-3-(3-bromophenyl)oxiranemethanolYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A magnetically stirred solution of m-chloroperbenzoic acid (3.57 g, 10.33 mmol) in dichloromethane (60.0 ml) at 25° C. was treated dropwise with a solution of trans-3-(3-bromophenyl)-2-propenol (2.0 g, 9.39 mmol) in dichloromethane (20.0 ml). After stirring for 16 h the mixture was diluted with dichloromethane (200 ml), washed with aqueous 1 M NaOH (2×200 ml), brine (2×200 ml) and dried (Na2SO4). Evaporation of the solvent in vacuo returned the crude eposide as a pale yellow oil (2.06 g). Column chromatography (ethyl acetate--light petroleum (b.p. 40-60° C.), 3:7) provided the title compound (1.53 g, 71%) as a pale yellow oil.

Workup

  1. washwashed with aqueous 1 M NaOH (2×200 ml), brine (2×200 ml)
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-aad9bb33bf5e44768c8034dfaa2ef5e5
Source dataset
uspto-grants-2000_12
Patent number
US06160120

Reaction notes

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