Hydrochloric Acid → HCID 117940420, compound

Temperature

-80 °C

Into a 200-mL three-neck flask was put 3.0 g (9.0 mmol) of 4,4′-bidibenzofuran, and the air in the flask was replaced with nitrogen. To this flask was added 45 mL of THF to dissolve 4,4′-bidibenzofuran, and the mixture was cooled down to −80° C. Then, 5.6 mL (9.0 mmol) of n-butyllithium (a 1.6 mol/L hexane solution) was dripped into this solution with a syringe. After that, the mixture solution was stirred for 2 hours while its temperature was increased to room temperature. After the stirring, this solution was cooled down to −80° C. Then, a solution in which 2.5 g (10 mmol) of iodine had been dissolved in 20 mL of THF was dripped into this solution with a dripping funnel, and the mixture was stirred for 18 hours while its temperature was returned to room temperature. After the stirring, approximately 10 mL of dilute hydrochloric acid (1.0 mol/L) was added to this solution, and the mixture was stirred for 2 hours. After the stirring, an aqueous layer of the mixture was extracted with ethyl acetate, and the extracted solution and an organic layer of the mixture were combined and washed with a saturated solution of sodium hydrogen carbonate and saturated brine. The organic layer was dried with magnesium sulfate and gravity-filtered. The obtained filtrate was concentrated to give a light brown solid. The obtained solid was purified by HPLC and washed with toluene to give 2.2 g of white powder, which was an objective substance, in 53% yield. Synthesis Scheme (c-2) of Step 2 is shown below.

1. customInto a 200-mL three-neck flask was put
2. temperaturewas increased to room temperature
3. temperatureAfter the stirring, this solution was cooled down to −80° C
4. customwas dripped into this solution with a dripping funnel
5. stirringthe mixture was stirred for 18 hours while its temperature
6. customwas returned to room temperature
7. stirringthe mixture was stirred for 2 hours
8. extractionAfter the stirring, an aqueous layer of the mixture was extracted with ethyl acetate
9. washwashed with a saturated solution of sodium hydrogen carbonate and saturated brine
10. dry with materialThe organic layer was dried with magnesium sulfate
11. filtrationgravity-filtered
12. concentrationThe obtained filtrate was concentrated
13. customto give a light brown solid
14. customThe obtained solid was purified by HPLC
15. washwashed with toluene

ORD record

ord-6835ba7cbb4f4a859cdf38218bb579ec

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09312498B2