Boron trifluoride etherate → (2,6-Dichloropyridin-3-yl)methanol

To a solution of 2,6-dichloronicotinic acid (1 g, 5.2 mmol) in THF (10 mL) was added NaBH4 (591 mg, 15.6 mmol) at 0° C. The mixture was stirred for 30 min and then BF3.OEt2 (2.2 g, 15.6 mmol) was added drop wise at 0° C. After addition was complete, the mixture was stirred at room temperature for 10 hr, until the reaction was completed. The reaction mixture was quenched by the addition of saturated NH4Cl solution (50 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the desired product as a white solid which was used in next step without further purification. (820 mg, Yield 80%).

1. additionAfter addition
2. stirringthe mixture was stirred at room temperature for 10 hr, until the reaction
3. customThe reaction mixture was quenched by the addition of saturated NH4Cl solution (50 mL)
4. extractionextracted with ethyl acetate (3×30 mL)
5. washThe combined organic layers were washed with brine (30 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-67342facce66438aa09bd70b55ba51f3

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906900B2