2-Chloroethyl chloroformate → HCID 68002661, compound

To a stirred solution of 4-Bromo-3-methoxy-aniline (10.0 g) in acetonitrile (176 mL) was added Hünig Base (25 mL) and 2-chloroethyl chloroformate (10.6 g). The mixture was stirred at room temperature for 0.5 h. The solvent was removed in vacuum. The residue was dissolved in tetrahydrofurane (250 mL), and potassium tert-butoxide (16.2 g) was added. The mixture was stirred at room temperature for 2 h. The solvent was removed in vacuum. The residue was dissolved in ethyl acetate and the mixture was washed with water and with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave a compound that was crystallized from ethanol. Yield: 7.7 g of the title compound. The mother liquor was concentrated in vacuum and aminophase-silica-gel chromatography gave a solid that was recrystallized from ethanol to give further 2.3 g of the title compound.

1. customThe solvent was removed in vacuum
2. dissolutionThe residue was dissolved in tetrahydrofurane (250 mL)
3. additionpotassium tert-butoxide (16.2 g) was added
4. stirringThe mixture was stirred at room temperature for 2 h
5. customThe solvent was removed in vacuum
6. dissolutionThe residue was dissolved in ethyl acetate
7. washthe mixture was washed with water and with saturated sodium chloride solution
8. dry with materialdried (sodium sulfate)
9. customthe solvent was removed in vacuum
10. customSilica gel chromatography gave a compound that
11. customwas crystallized from ethanol
12. concentrationThe mother liquor was concentrated in vacuum and aminophase-silica-gel chromatography
13. customgave a solid
14. customthat was recrystallized from ethanol

ORD record

ord-21cd23f96f004b469e229def0205af21

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388177B2