1,3-Dibromopropane → HCID 23384157, compound

Temperature

-70 °C

To a solution of 1.5 molar LDA in cyclohexane (60 mmol, 40 mL) cooled to −70° C. was added a solution of cyclopentane carboxylic acid methyl ester (42 mmol, 5.6 g) in THF (15 mL) over 30 min. The mixture was stirred for 1 hr at −70° C. Then a solution of 1,3-dibromopropane (60 mmol, 11.9 g) in THF (30 mL) which had been pre-cooled to −70° C. was added all at once and the reaction mixture was stirred at −70° C. for one hr then at room temperature overnight. The reaction mixture was poured into brine (200 mL), the layers were separated, the aqueous layer was extracted with ether (3×30 mL) and the combined organic layers were washed with brine (20 mL), dried (magnesium sulfate) and concentrated to give a yellow oil (15 g). Distillation through a short path apparatus with a 3′ vigreux column gave a yellow oil, 7.96 g (76%), bp 76-80° C. at 0.3 mm.

1. additionwas added all at once and the reaction mixture
2. stirringwas stirred at −70° C. for one hr
3. customat room temperature
4. customovernight
5. customthe layers were separated
6. extractionthe aqueous layer was extracted with ether (3×30 mL)
7. washthe combined organic layers were washed with brine (20 mL)
8. dry with materialdried (magnesium sulfate)
9. concentrationconcentrated

ORD record

ord-b5e52d2579bb41c1b50fadaf2e24499e

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806365B2