1,6-Dibromohexane → HCID 67540595, compound

A suspension of 37 (7.13 g, 41.22 mmol) and NaOH (1.52 g, 38.10 mmol) in acetonitrile (309 ml) was stirred under reflux for 1 h before 1,6-dibromohexane (2.51 g, 10.31 mmol) was added in one portion. The reaction mixture was stirred under reflux for another 22 hours before the precipitates were removed by filtration. The filtrate was quenched with water and extracted with methylene chloride. The extracts were combined, washed with water and dried over MgSO4. Upon evaporating off the solvent, the crude product was purified by gradient column chromatography on silica gel with hexanes/ethyl acetate 19:1 to 9:1 (v/v) as the eluent to yield 38 (4.02 g, 91%) as a white powder. 1H NMR (400 MHz, CDCl3, 298 K): δ(ppm) 7.15-7.11 (m, 2H), 7.07-7.04 (m, 4H), 6.83-6.80 (m, 2H), 3.96-3.93 (t, 4H), 1.82-1.79 (t, 4H), 1.55-1.51 (m, 4H).

1. additionwas added in one portion
2. stirringThe reaction mixture was stirred
3. temperatureunder reflux for another 22 hours before the precipitates
4. customwere removed by filtration
5. customThe filtrate was quenched with water
6. extractionextracted with methylene chloride
7. washwashed with water
8. dry with materialdried over MgSO4
9. customUpon evaporating off the solvent
10. customthe crude product was purified by gradient column chromatography on silica gel with hexanes/ethyl acetate 19:1 to 9:1 (v/v) as the eluent

ORD record

ord-dae38e799e4642c4bac27a70c50e36cf

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040718B2