Methanol → 1,3-Dioxane, 5-(2-bromoethyl)-2,2-dimethyl-

To an ice-cooled solution of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan (1.92 g, 12 mmol) and carbon tetrabromide (7.96 g, 24 mmol) in dimethylformamide (100 ml), triphenylphosphine (6.30 g, 24 mmol) was added and the solution was left at 4° C. overnight. To this solution methanol (20 ml) was added and the solvent was then evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane-acetone (12:1) to afford 5-(2-bromoethyl)-2,2-dimethyl-1,3-dioxan as a clear colourless liquid (0.89 g, 40%); νmax (film) 2940, 1370, 1270, 1260, 1200, and 1070 cm-1 ; δH (CDCl3) 1.42 (6 H, s, C(CH3)2), 1.94 (3 H, m, CHCH2CH2Br), 3.43 (2 H, t, J 7 Hz, CH2Br), and 3.5-4.1 (4 H, m, 2×CH2O); (Found: C, 42.84; H, 6.93%. C8H15BrO2 requires: C, 43.07; H, 6.78%. [M-CH3 ]+ found 207.0024; C7H12BrO2 requires 207.0021).

1. additionwas added
2. customthe solvent was then evaporated under reduced pressure
3. customThe residue was purified by column chromatography on silica gel
4. washeluting with hexane-acetone (12:1)

ORD record

ord-1b78e368e9e7479bb740a0c997d8fec5

Source dataset

uspto-grants-1991_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05075445