3-Fluorosalicylaldehyde → 2-Fluoro-6-(1-hydroxyethyl)phenol
Reaction equation
[CH3:1][Li].[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=[O:8])[C:5]=1[OH:12]>C1COCC1>[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]([OH:8])[CH3:1])[C:5]=1[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl lithium (25.5 mL, 35.7 mmol, 1.4M in ether) was added to a cooled −78° C. solution of 3-fluorosalicylaldehyde (2 g, 14.3 mmol) dissolved in THF (50 mL). The reaction mixture was stirred for 3 hours and then warmed up to room temperature. After 3 hours the reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic extracts were washed with 1N HCl, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by flash column chromatography (0% to 20% EtOAc in hexanes) to give the title compound as a clear oil (2.2 g, 99%). 1H NMR (400 MHz, CDCl3): δ 1.58 (d, J=6.6 Hz, 3 H), 2.68 (s, 1 H), 5.13 (m, 1 H), 6.78 (td, J=7.8, 4.8 Hz, 1 H), 6.87 (d, J=7.6, 1 H), 6.99 (m, 1 H), 7.33 (s, 1 H).