Potassium Carbonate → 5-(4-Bromophenyl)-1,3-oxazole

HRID 1063892Notes

Reaction equation

HRID 1063892 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C1(C)C=CC(S([CH2:19][N+:20]#[C-:21])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]2[O:7][CH:21]=[N:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27764185-(4-Bromophenyl)-1,3-oxazoleYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromobenzaldehyde (5.00 g), p-toluenesulfonylmethyl isocyanide (5.43 g) and potassium carbonate (5.60 g) in methanol (50 ml) was heated under reflux for 2 hours. After evaporation of solvent, ethyl acetate and saturated ammonium chloride solution were added. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (2:1) to give 5-(4-bromophenyl)oxazole as a pale yellow powder (5.77 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent, ethyl acetate and saturated ammonium chloride solution
  4. additionwere added
  5. customThe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with a mixture of hexane and ethyl acetate (2:1)

Sources & evidence

ORD record
ord-0ff63b8c6a96497ab74f9906123bf40e
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

Loading…