Methyl iodide → 3,5-Dibromo-4-methoxyaniline

4-Amino-2,6-dibromo-phenol (14.13 g, 52.9 mmol) was dissolved in acetone (425 mL) to give a dark brown solution. Potassium carbonate (21.95 g, 158.8 mmol) was added followed by iodomethane (3.46 mL, 55.6 mmol). The mixture was stirred at rt overnight. The acetone was removed under reduced pressure and the residue partitioned between EtOAc and water. Sodium metabisulphite and brine were added to aid separation of the layers. The mixture was extracted into EtOAc (4×150 mL). The combined organic layers were washed with sodium metabisuphite solution (saturated, aqueous) then brine, dried over Na2SO4 and concentrated under reduced pressure. A dark brown oil was obtained which crystallised upon standing. The mixture was purified by chromatography, Biotage SP4, 330 g Si cartridge, 20% EtOAc in cyclohexane. The relevant fractions were combined to give the desired compound as a brown solid, 11.31 g (76%). m/z: 280.03/282.00/284.02 [M+H]+.

1. customto give a dark brown solution
2. customThe acetone was removed under reduced pressure
3. customthe residue partitioned between EtOAc and water
4. additionSodium metabisulphite and brine were added
5. customseparation of the layers
6. extractionThe mixture was extracted into EtOAc (4×150 mL)
7. washThe combined organic layers were washed with sodium metabisuphite solution (saturated, aqueous)
8. dry with materialbrine, dried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customA dark brown oil was obtained which
11. customcrystallised
12. customThe mixture was purified by chromatography, Biotage SP4, 330 g Si cartridge, 20% EtOAc in cyclohexane

ORD record

ord-0915e05875a64659a5f553bdcbc0d652

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181234B2