2-(Ethylthio)ethanol → 7-Oxa-10-thiadodecyl bromide

NaH (1.85 g, 0.046 mol) was washed with hexane and then suspended in dry THF (60 mL). 3-Thiapentane-1-ol (4.67 g, 0.04 mol) in THF (20 mL) was added and stirred for 1 h at room temperature. 1,6-Dibromohexane (9.76 g, 0.04 mol) in THF (20 mL) was added and the mixture was refluxed for 20 h. After evaporation of the solvent, the residue was dissolved in ethyl acetetate (200 mL). The organic phase was washed with water (2×50 mL), and dried (Na2SO4). The crude product was purified by Kugelrohr distillation to give 7-oxa-10-thiadodecyl bromide (3.34 g, 31%); bp 48° C. -56° C./0.04 torr; NMR: 1.25 (3H, t, J=7 Hz), 1.2-1.9 (8H, m), 2.59 (2H, q, J=7 Hz), 2.68 (2H, t, J=7 Hz), and 3.2-3.7 ppm (6H, m).

1. temperaturethe mixture was refluxed for 20 h
2. customAfter evaporation of the solvent
3. dissolutionthe residue was dissolved in ethyl acetetate (200 mL)
4. washThe organic phase was washed with water (2×50 mL)
5. dry with materialdried (Na2SO4)
6. distillationThe crude product was purified by Kugelrohr distillation

ORD record

ord-0bc4080f589c46c6b3168e1ae7d72fb7

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05082967