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

To a solution of 4-trifluoromethoxybenzaldehyde (215.0 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 (402.0 g, 2.26 mol) in equal portions over seven hours. The reaction mixture was stirred for four days at room temperature, poured into ice-water and extracted with CH2Cl2. The organic layer was washed with water and subsequently treated with saturated NaHCO3 (1.5 L) for two hours. 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. additionsubsequently treated with saturated NaHCO3 (1.5 L) for two hours
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-a0c6cd4e3c5d49158be4f08f4d61f8d3

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071218B2