Water → Methyl 5-bromo-2-ethylbenzoate

The above methyl 2-ethylbenzoate was mixed with molecular sieve 13× (powder, 70 g), and while stirring the mixture, bromine (5.2 ml) was added dropwise thereto at 80° C. The mixture was further stirred at the same temperature for 1.5 hours. The mixture was cooled to room temperature, and added thereto were potassium carbonate (7.4 g), water (70 ml) and methanol (350 ml), and the mixture was stirred for 8 hours. Insoluble materials were filtered off, and suspended in a mixed solution of methanol (500 ml)-water (500 ml), and the mixture was stirred at room temperature overnight. Insoluble materials were filtered off and the filtrate was combined with the previously obtained filtrate, and the solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was distilled under reduced pressure, to give methyl 5-bromo-2-ethylbenzoate (2.44 g). APCI-Mass m/Z 260/262 (M+NH4).

1. additionwas added dropwise
2. customat 80° C
3. additionadded
4. stirringthe mixture was stirred for 8 hours
5. filtrationInsoluble materials were filtered off
6. stirringthe mixture was stirred at room temperature overnight
7. filtrationInsoluble materials were filtered off
8. customthe solvent was evaporated under reduced pressure
9. extractionThe residue was extracted with ethyl acetate
10. washthe extract was washed with brine
11. dry with materialdried over sodium sulfate
12. customThe solvent was evaporated under reduced pressure
13. distillationthe residue was distilled under reduced pressure

ORD record

ord-5298ee4340694589aa50a170c4ea29cc

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785403B2