Chloroform → HCID 10560429, compound

Temperature

0 °C

To a stirred solution of 4-chloro-2,6-bis(hydroxymethyl)pyridine (2.41 g, 13.93 mmol) and triethylamine (7.8 ml, 55.72 mmol) at 0° C. in 100 ml of anhydrous dichloromethane and 50 ml of anhydrous chloroform under an argon atmosphere was added methanesulfonyl chloride (3.2 ml, 41.79 mmol). The solution was stirred at 0° C. for 30 minutes, warmed to room temperature and stirred a further 36 hours. The reaction mixture was quenched with water (50 ml), the aqueous phase extracted with dichloromethane, dried (MgSO4) and concentrated in vacuo to afford a red-orange oil. The residual oil was passed through a short plug of silica gel using dichioromethane as eluent thus affording after concentration a pale yellow solid which was identified by 1H NMR as 4-chloro-2,6-bis-(chloromethyl)pyridine (1.9 g, 65%).

1. temperaturewarmed to room temperature
2. stirringstirred a further 36 hours
3. customThe reaction mixture was quenched with water (50 ml)
4. extractionthe aqueous phase extracted with dichloromethane
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo
7. customto afford a red-orange oil
8. customthus affording
9. concentrationafter concentration a pale yellow solid which

ORD record

ord-0aaeddb2be884899971dcf6fe8225ddb

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05698546