Thionyl bromide → 4-(Bromomethyl)-3,5-difluoropyridine

(3,5-Difluoro-4-pyridyl)methanol (6.11 g, 42.11 mmol) was dissolved in CH2Cl2 (140 mL). At 0° C. Thionyl bromide (3.589 mL, 46.32 mmol) was added slowly, then 1 drop of DMF was added: the solution turned yellow with gas evolution. The reaction mixture was stirred at rt for 1.5 h. It was quenched with 10 ml water. The pH was made basic (pH=9) with aq NaHCO3. The water layer was extracted 3 times with CH2Cl2. The combined organic layers were washed with brine. The organic phase was dried with Na2SO4, filtrated and the filtrate evaporated. The desired product was obtained as a brown liquid (9.68 g, lacrimator).

1. customAt 0° C
2. customIt was quenched with 10 ml water
3. extractionThe water layer was extracted 3 times with CH2Cl2
4. washThe combined organic layers were washed with brine
5. dry with materialThe organic phase was dried with Na2SO4
6. filtrationfiltrated
7. customthe filtrate evaporated

ORD 기록

ord-ea3b8cd878e34e4f8bdae6b7f8cf2e5c

출처 데이터셋

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09040708B2