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

HRID 512688Notes

Reaction equation

HRID 512688 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-d530a173e83047f19c37e048a5ee7b82
Source dataset
uspto-grants-2015_08
Patent number
US09102643B2

Reaction notes

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