Bromine → 2-(Benzyloxy)-5-(2-oxiranyl)benzamide

HRID 1281476Notes

Reaction equation

HRID 1281476 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])(=[O:3])[CH3:2].BrBr>C(Cl)(Cl)Cl>[CH2:14]([O:13][C:7]1[CH:6]=[CH:5][C:4]([CH:1]2[CH2:2][O:3]2)=[CH:12][C:8]=1[C:9]([NH2:11])=[O:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 24408Bromine4×HCID 30186095-Acetyl-2-(phenylmethoxy)benzamide

Product 1

HCID 99035062-(Benzyloxy)-5-(2-oxiranyl)benzamideYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Acetyl-2-(phenylmethoxy)benzamide (10.0 g, 37.1 mmol) was dissolved in chloroform and brought to reflux. Bromine (1.98 g, 12.4 mmol) was added. The solution was allowed to cool to room temperature. After 10 minutes the bromine color had disappeared and a second portion of bromine was added. A third portion of bromine was added after the color had again discharged and the solution refluxed for a further 10 minutes. The flask was allowed to cool and placed in the freezer overnight. The solvent was removed in vacuo and the residue crystallized from ethanol to provide the title compound (11.3 g, 32.4 mmol).

Workup

  1. temperatureto reflux
  2. temperaturethe solution refluxed for a further 10 minutes
  3. temperatureto cool
  4. customplaced in the freezer overnight
  5. customThe solvent was removed in vacuo
  6. customthe residue crystallized from ethanol

Sources & evidence

ORD record
ord-08ceacb805af4081aa0a37e7e9a90372
Source dataset
uspto-grants-2002_09
Patent number
US06451814B1

Reaction notes

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