1,5-Dibromopentane → HCID 22115197, compound

To a stirred solution of 1,5-dibromopentane (23.00 g, 0.1 mol) in THF (100 ml) at -60° C. under N2, was slowly added, during 30 min., 100 ml (0.10 mol) of a 1.0M solution of 2-thienyllithium in THF (Aldrich). Stirring was continued for 1 h at -60° C. After gradual warming to room temperature, the mixture was stirred for 2 h and slowly poured over a bed of ice (ca. 200 g). The organic layer was separated and the aqueous layer was extracted with Et2O (2×100 ml). The combined organic layer and the extracts were washed with saturated NaCl solution (2×75 ml), dried (MgSO4) and concentrated to a dark oil (23.13 g). Fractional distillation gave 12.34 g (53%) of 1-bromo-5-(2-thienyl) pentane as a colorless oil, b.p. 87°-88° C. (0.7 mm); nD23 1.5440.

1. stirringthe mixture was stirred for 2 h
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with Et2O (2×100 ml)
4. washThe combined organic layer and the extracts were washed with saturated NaCl solution (2×75 ml)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated to a dark oil (23.13 g)
7. distillationFractional distillation

ORD record

ord-54e7b01878034ee3abe34e894722b05f

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05104885