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

HRID 56589Notes

Reaction equation

HRID 56589 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-013b8f9ce8de44c2aae86244c072976b
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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