Sulfuric Acid → 3-Bromo-4-(trifluoromethoxy)benzaldehyde

To a solution of 4-trifluoromethoxybenzaldehyde (215 g, 1.13 mol) in a mixture of TFA (300 mL), CH2Cl2 (300 mL) and H2SO4 (150 mL) was added at room temperature N-bromosuccinimide (402 g, 2.26 mol) in equal portion over 7 hours. The reaction mixture was stirred for 4 days at room temperature, poured into ice-water and extracted with CH2Cl2. The organic layer was washed with water then treated with saturated NaHCO3 (1.5 L) for 2 hrs. The layers were separated and the organic layer further washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was triturated with hexane and filtered. After evaporation of the solvent, the residue was distilled to give 3-bromo-4-trifluoromethoxybenzaldehyde (190.2 g, 81° C., 1.0 mm/Hg, 62%).

1. extractionextracted with CH2Cl2
2. washThe organic layer was washed with water
3. additionthen treated with saturated NaHCO3 (1.5 L) for 2 hrs
4. customThe layers were separated
5. washthe organic layer further washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customThe residue was triturated with hexane
10. filtrationfiltered
11. customAfter evaporation of the solvent
12. distillationthe residue was distilled

ORD record

ord-da67f034cfcc4f1599f3d74c4a7f7bee

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06515003B1