3-Fluoropyridine-4-carboxylic acid → (3-Fluoropyridin-4-yl)methanol

Temperature

0 °C

At 0° C. LAH (200 mg, 4 eq.) was added to 3-fluoro-isonicotinic acid (186 mg, 1.32 mmol, 1 eq.) suspension in 25 mL THF. The reaction was stirred at 0° C. for 1 hour. The reaction was quenched by adding 0.2 mL water, followed by 0.4 mL 10% NaOH aqueous solution and 0.6 mL water at 0° C. Ethyl acetate was added to the reaction crude and washed with brine. n-Butanol was used to extract back from the brine. The organic layers were combined and concentrated down and purified (silica gel, 0-15% MeOH/DCM) to give colorless oil (78 mg, 46%). 1H NMR (300 MHz, CD3OD): δ 8.39 (m, 2H), 7.61 (m, 1H), 4.86 (s, 2H).

1. customAt 0° C
2. customThe reaction was quenched
3. additionby adding 0.2 mL water
4. customfollowed by 0.4 mL 10% NaOH aqueous solution and 0.6 mL water at 0° C
5. additionEthyl acetate was added to the reaction crude
6. washwashed with brine
7. extractionto extract back from the brine
8. concentrationconcentrated down
9. custompurified (silica gel, 0-15% MeOH/DCM)

ORD record

ord-35baa30d33d5443fabafc863463a326a

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106064B2