1,3-Dibromopropane → HCID 70008734, compound

Temperature

5 °C

In a stream of nitrogen, 100 ml of a dimethylformamide (to be referred to as DMF hereinafter) solution containing 20.03 g (115.8 mmol) of 3-bromophenol was cooled to 5° C. and mixed with 4.9 g (122 mmol) of 60% sodium hydride. After 1 hour of stirring at room temperature, this was mixed with 25 ml of a DMF solution containing 11.5 g (57 mmol) of trimethylene dibromide and stirred at 70° C. for 20 hours. The reaction solution was extracted with 800 ml of ethyl acetate and washed with water (200 ml, 5 times) and saturated brine (100 ml, twice). The organic layer was dried with anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure. By purifying the residue by a silica gel column chromatography, 13.70 g (yield 62%) of the title compound was obtained as a colorless oil.

1. stirringstirred at 70° C. for 20 hours
2. extractionThe reaction solution was extracted with 800 ml of ethyl acetate
3. washwashed with water (200 ml, 5 times) and saturated brine (100 ml
4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
5. customthe solvent was evaporated under a reduced pressure
6. customBy purifying the residue by a silica gel column chromatography

ORD record

ord-7d31c4004ef04646aa00d7e55ccb6255

Source dataset

uspto-grants-2001_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06333291B1