Trimethylamine oxide → 2-Bromo-5-(2-pyrimidinyl)benzaldehyde
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH2:14]Br.C[N+]([O-:20])(C)C>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH:14]=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
To a solution of 1.75 g of the crude title compound of Step D in 6 mL of anhydrous dimethylsulfoxide ("DMSO") under argon, 3.0 g of anhydrous trimethylamine N-oxide (prepared as described in Soderquist et al., Tet. Letters., 27, 3961 (1986); this compound is also commercially available) were added and the mixture stirred at 55° C. for 12 hrs. The mixture was then cooled and added to 100 mL of ice/water and extracted with 3×50 mL of EtOAc. The combined organic extracts were washed once with 100 mL of brine and dried and evaporated. The residue was chromatographed on 100 mL of silica gel using Hexanes/EtOAc 6:1 to afford 0.86 g (81.5% for two steps) of the title compound of this step as a white solid.
Workup
- additionwere added
- temperatureThe mixture was then cooled
- extractionextracted with 3×50 mL of EtOAc
- washThe combined organic extracts were washed once with 100 mL of brine
- customdried
- customevaporated
- customThe residue was chromatographed on 100 mL of silica gel
Sources & evidence
- ORD record
- ord-a3a3ecffda364657bf34d46f5f1333ab
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05780473
Reaction notes
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