4-Bromo-3,5-dimethoxybenzaldehyde → 5-(4-Bromo-3,5-dimethoxyphenyl)oxazole

HRID 2359248Notes

Reaction equation

HRID 2359248 reaction equation
[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].C1(C)C(S([CH2:23][N+:24]#[C-:25])(=O)=O)=CC=CC=1>CO>[Br:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([C:6]2[O:7][CH:25]=[N:24][CH:23]=2)=[CH:4][C:3]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 30155794-Bromo-3,5-dimethoxybenzaldehydeHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 584321505-(4-Bromo-3,5-dimethoxyphenyl)oxazoleYield 39%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-bromo-3,5-dimethoxybenzaldehyde (5.04 g, 20.57 mmole) and toluenesulfonylmethyl isocyanide (4.22 g, 21.6 mmole) in MeOH (50 ml) was heated at reflux for 3 hrs. After evaporation to near dryness, H2O (50 ml) and EtOAc (200 ml) were added with stirring. The organic layer was separated and washed with brine (50 ml), dried over Na2SO4 and concentrated in vacuo. Et2O (50 ml) was added with swirling and the product was collected by filtration, washed with Et2O (2×25 ml) and dried giving 5-(4-bromo-3,5-dimethoxyphenyl)oxazole as a pale yellow solid (2.25 g, 39% yield).

Workup

  1. temperatureat reflux for 3 hrs
  2. customAfter evaporation
  3. additionwere added
  4. customThe organic layer was separated
  5. washwashed with brine (50 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. additionEt2O (50 ml) was added
  9. filtrationthe product was collected by filtration
  10. washwashed with Et2O (2×25 ml)
  11. customdried

Sources & evidence

ORD record
ord-8b2114be12b3483d9f092f65af499264
Source dataset
uspto-grants-2014_04
Patent number
US08685975B2

Reaction notes

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