Ethanol → HCID 58852670, compound

Temperature

0 °C

113 ml (340 mmol) of a 3M methylmagnesium chloride solution in THF were added dropwise with vigorous stirring to a suspension, cooled to −78° C., of 102.6 g (300 mmol) of di(6-bromo-2-pyridyl)ketone in 1000 ml of THF at such a rate that a temperature of −60° C. was not exceeded. When the addition was complete, the mixture was stirred for a further 30 min., then 50 ml of ethanol were added dropwise, the mixture was warmed to 0° C., and 60 ml of semi-saturated ammonium chloride solution were added. The reaction mixture was filtered, the salts were washed twice with 100 ml of THF each time, and the filtrate was evaporated to dryness in a rotary evaporator. The oily residue was taken up in 1000 ml of dichloromethane, and the organic phase was washed three times with 300 ml of water and dried over magnesium sulfate. Stripping off of the dichloromethane left 106.0 g (296 mmol), corresponding to a yield of 98.6%, of the crude product having a purity of about 95% according to 1H-NMR as a yellow-brown oil, which was reacted further without purification.

1. additionWhen the addition
2. stirringthe mixture was stirred for a further 30 min.
3. filtrationThe reaction mixture was filtered
4. washthe salts were washed twice with 100 ml of THF each time
5. customthe filtrate was evaporated to dryness in a rotary evaporator
6. washthe organic phase was washed three times with 300 ml of water
7. dry with materialdried over magnesium sulfate
8. waitleft 106.0 g (296 mmol)
9. customwas reacted further without purification

ORD record

ord-5f9605cc5b344a41938476ad3916eba2

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029539B2