2-Amino-2-methyl-1-propanol → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

4-Bromobenzoyl chloride (20.02 g, 91 mmol) was dissolved in dichloromethane (180 ml) and added dropwise to a solution of 2-amino-2-methyl-1-propanol (19.20 g, 216 mmol) in dichloromethane (90 ml) at ambient temperature. The mixture was stirred for 24 hours at ambient temperature, followed by filtration and removal of the solvent at reduced pressure. Thionyl chloride (90 ml) was added dropwise and the mixture was stirred for 30 minutes at ambient temperature. Excess thionyl chloride was removed at reduced pressure and the residue was added to an aqueous HCl-solution (5%, 500 ml). The solution was washed with ether (2×100 ml) and aqueous NaOH (50%) was added to pH 9. The basic solution was extracted with ether (3×100 ml), and the combined ether solution was washed with water (50 ml) and saturated aqueous NaCl-solution. The dried (MgSO4) ether solution was evaporated and the title compound isolated by distillation. Yield 14.14 g (61%), b.p. 128-130° C. (1 mm Hg).

1. filtrationfollowed by filtration and removal of the solvent at reduced pressure
2. additionThionyl chloride (90 ml) was added dropwise
3. stirringthe mixture was stirred for 30 minutes at ambient temperature
4. customExcess thionyl chloride was removed at reduced pressure
5. additionthe residue was added to an aqueous HCl-solution (5%, 500 ml)
6. washThe solution was washed with ether (2×100 ml) and aqueous NaOH (50%)
7. additionwas added to pH 9
8. extractionThe basic solution was extracted with ether (3×100 ml)
9. washthe combined ether solution was washed with water (50 ml) and saturated aqueous NaCl-solution
10. dry with materialThe dried (MgSO4) ether solution
11. customwas evaporated

ORD record

ord-429695a861be41c1a905a0d93060b735

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06117412