5-(Bromoacetyl)-2-(phenylmethoxy)benzamide → 2-(Benzyloxy)-5-(2-oxiranyl)benzamide

HRID 395968Notes

Reaction equation

HRID 395968 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19]Br)=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>O1CCCC1.C(O)C>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][O:21]2)=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 30183385-(Bromoacetyl)-2-(phenylmethoxy)benzamideHCID 4311764Sodium borohydride

Product 1

HCID 99035062-(Benzyloxy)-5-(2-oxiranyl)benzamideYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(Benzyloxy)-5-(2-bromoacetyl)benzamide (11.3 g, 32.30 mmol) was dissolved in anhydrous tetrahydrofuran (250 mL) and cooled in an ice bath. The solution was diluted with ethanol (250 mL). Sodium borohydride (1.2 g, 32.3 mmol) was added in three portions. Following addition the solvent was removed in vacuo and the residue partitioned between water and ethyl acetate. The organic layer was washed with water, brine, and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo to yield crude title compound (10.88 g, 31.06 mmol).

Workup

  1. temperaturecooled in an ice bath
  2. additionaddition the solvent
  3. customwas removed in vacuo
  4. customthe residue partitioned between water and ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe solution was filtered
  8. customthe solvent evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-a04e68789ec346debfa53c0fffa2e7fe
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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