3-Fluorobenzaldehyde → 3-Fluorobenzylic alcohol

A freshly oven dried 250 mL round-bottom flask was charged with 2-iodo-3-nitro-5-chloro-pyridine (1.41 g, 5.0 mmol). The resultant solution was cooled to −78° C. under N2 and PhMgCl (2 M, 3 mL, 6.0 mmol) added and then stirred at the same temperature for 30 min. 3-Fluorobenzaldehyde (1.24 g, 10 mmol) was added and the resulting mixture stirred at −78° C. for two hours and then at room temperature for 24 h. The reaction was quenched with NH4Cl (sat), extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was further purified through automated normal-phase chromatography to afford 5-chloro-3-nitropyridin-2-yl)(3-fluorophenyl)methanol (560 mg, 40%) which was used directly for the next step: 1H NMR (400 MHz, CDCl3) δ 8.85 (d, 1 H), 8.37 (d, 1 H), 7.23 (m, 1 H), 7.06 (dd, 1 H), 6.95 (dd, 1 H), 6.43 (d, 2H), 4.99 (d, 1 H); MS (ES) (M+−OH) expect 265.0, found 265.1.

1. customA freshly oven dried 250 mL round-bottom flask
2. stirringthe resulting mixture stirred at −78° C. for two hours
3. waitat room temperature for 24 h
4. customThe reaction was quenched with NH4Cl (sat)
5. extractionextracted with EtOAc
6. washwashed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated under reduced pressure
9. customThe residue was further purified

ORD record

ord-5b312d4fd6804d1796953dc4dcf76a16

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622583B2