Potassium Carbonate → 2-(4-Nitrophenyl)oxirane

HRID 387228Notes

Reaction equation

HRID 387228 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8](=[O:11])[CH2:9]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]2[CH2:9][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 668402-Bromo-4'-nitroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 922282-(4-Nitrophenyl)oxiraneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
2.5 °C

Procedure

To an ice-cold stirred suspension of 4-nitrophenacyl bromide (80 g, 0.33 mol) in methanol (800 mL) was added sodium borohydride (13.64 g, 0.36 mol) in small portions. After stirring for 2 h at 0-5° C., potassium carbonate (45.20 g, 0.33 mol) was added in small portions at the same temperature. The suspension was stirred for 18 h at room temperature, diluted with brine (600 mL) and extracted with diethyl ether (600 mL, 500 mL), the combined organic layers were dried over sodium sulfate, filtered and evaporated. The title compound (54.87 g, 0.33 mmol, 100%) was obtained as a pale yellow solid.

Workup

  1. stirringThe suspension was stirred for 18 h at room temperature
  2. extractionextracted with diethyl ether (600 mL, 500 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ce75885e707e433d8f5ee23e443ec10f
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

Loading…