Dimethylformamide → Benzene, ((5-bromopentyl)oxy)-

To a well-stirred suspension of sodium hydride (15.3 g, 0.32 mol; 50% oil dispersion) in dry DMF (500 ml) containing (25 g, 0.26 mol), was added dropwise 1,5-dibromopentane (122.3 g, 0.53 mol). After the addition was complete, the reaction mixture was stirred at 60°-70° C. for 4 hours. Most of the DMF was next removed under reduced pressure, and the residue was dissolved in ethyl acetate (250 ml). The organic extract was washed successively with a 5% sodium hydroxide solution, water and brine. After drying the organics over anhydrous magnesium sulfate, all volatiles were removed. The residual yellow liquid was then distilled under reduced pressure, and the pure product was collected at 118°-125° C./1 mm as a clear colorless liquid (26 g, 40% yield).

1. additioncontaining (25 g, 0.26 mol)
2. additionAfter the addition
3. customMost of the DMF was next removed under reduced pressure
4. dissolutionthe residue was dissolved in ethyl acetate (250 ml)
5. extractionThe organic extract
6. washwas washed successively with a 5% sodium hydroxide solution, water and brine
7. dry with materialAfter drying the organics over anhydrous magnesium sulfate
8. customall volatiles were removed
9. distillationThe residual yellow liquid was then distilled under reduced pressure

ORD record

ord-1b25fdc1eb6a49038b2c0aedae98576d

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04794188