2,6-Dibromoaniline → HCID 57678304, compound

Temperature

60 °C

2,6-Dibromoaniline (1.0 g, 3.98 mmol) was dissolved in dioxane (20 mL) and treated with diisopropylethylamine (1.39 mL, 7.96 mmol) followed by 4-tert-Butylbenzoyl chloride (1.70 g, 7.96 mmol). The solution was warmed to 60° C. and stirred overnight. The mixture was concentrated under reduced pressure and the residue was re-dissolved in ethyl acetate (50 mL). The organic solution was washed with 10% HCl (2×50 mL), saturated sodium carbonate (50 mL) and saturated sodium chloride (50 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography, eluting with 20% acetone/hexane to yield 1.33 g (81%) of product. MS (ESI) m/z 409.9772; HPLC Method B, purity 92.3% at 210-370 nm, 10.4 min.; 89.7% at 232 nm, 10.4 min.; HRMS: calcd for C17H17Br2NO+H+, 409.97496; found (ESI, [M+H]+), 409.9772.

1. concentrationThe mixture was concentrated under reduced pressure
2. dissolutionthe residue was re-dissolved in ethyl acetate (50 mL)
3. washThe organic solution was washed with 10% HCl (2×50 mL), saturated sodium carbonate (50 mL) and saturated sodium chloride (50 mL)
4. dry with materialThe organic layer was dried (magnesium sulfate)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash silica gel chromatography
8. washeluting with 20% acetone/hexane

ORD record

ord-f6ae222480e640beabfa5ab9d46c5ab1

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531542B2