Hydrochloric Acid → (2-Chloro-4-fluoro-5-nitrophenyl)methanol

To a solution of 10.8 g (0.053 mole) of 2-chloro-4-fluoro-5-nitrobenzaldehyde in 100 ml of tetrahydrofuran was added 0.50 g (0.013 mole) of sodium borohydride portionwise. The reaction mixture was stirred for one hour after which dilute hydrochloric acid was added to destroy unreacted sodium borohydride. To this mixture was added 200 ml of methylene chloride, and the phases were separated. The organic phase was washed three times with water, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving a residue weighing 10.7 g. This residue was combined with 1.67 g of a similar residue another run of the same reaction. The combined residues were passed through a silica gel column, eluting with ethyl acetate/heptane (1/4) to yield 7.7 g of 2-chloro-4-fluoro-5-nitrobenzyl alcohol as a yellow solid.

1. additionwas added
2. customto destroy unreacted sodium borohydride
3. additionTo this mixture was added 200 ml of methylene chloride
4. customthe phases were separated
5. washThe organic phase was washed three times with water
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. customThe solvent was evaporated from the filtrate under reduced pressure
9. customleaving a residue
10. customanother run of the same reaction
11. washeluting with ethyl acetate/heptane (1/4)

ORD record

ord-ef30e54f9f504dd79a79c8a1ed3a5323

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846882