tert-Butyl methyl ether → HCID 19777981, compound

Temperature

70 °C

To a stirred solution of 4-methyl-2-nitro-benzoic acid methyl ester (108.5 g, 555.7 mmol) in acetonitrile (750 mL), was added NBS (97.9 g, 550.1 mmol). The mixture was heated to a gentle reflex with a 200 W light bulb on for 5.5 hours. The solvent was evaporated, and the residue was dissolved in ethyl acetate (1500 mL). The solution was washed with water (2×600 mL) and brine (300 mL), dried over magnesium sulfate, and concentrated to give a brown oil. To the oil, was added t-butyl methyl ether (300 mL). The mixture was heated at 70° C. for 15 minutes. The mixture was allowed to cool to about 53° C. over one hour, then to 45° C., and then at 20-25° C., while blowing nitrogen with a glass pipette overnight. The suspension was filtered via a medium pore-sized funnel. The solid was washed with a pre-cooled 10° C. mixed solvent of heptane/MTBE (1/2 vol/vol) and suction dried in hood overnight to give 4-bromomethyl-2-nitro-benzoic acid methyl ester as an off-white solid (66 g, 43% yield). The solid was used in the next step without further purification.

1. temperatureThe mixture was heated to a gentle reflex with a 200 W light bulb on for 5.5 hours
2. customThe solvent was evaporated
3. dissolutionthe residue was dissolved in ethyl acetate (1500 mL)
4. washThe solution was washed with water (2×600 mL) and brine (300 mL)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customto give a brown oil
8. temperatureto cool to about 53° C. over one hour
9. customto 45° C.
10. customat 20-25° C.
11. customwith a glass pipette overnight
12. filtrationThe suspension was filtered via a medium pore-sized funnel
13. washThe solid was washed with a pre-cooled 10° C.
14. additionmixed solvent of heptane/MTBE (1/2 vol/vol) and suction
15. customdried in hood overnight

ORD record

ord-7c0119402f754d51a03b25a51ce97468

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096573B2