Hydrochloric Acid → 3-Fluoro-4-nitrobenzyl alcohol

Participants

Reaction Steps

To an ice-cooled suspension of NaBH4 (204 mg, 5.4 mmol, 2 eq.) in THF (10 mL) was added dropwise 3-fluoro 4-nitro benzoic acid (500 mg, 2.7 mmol, 1 eq.) in THF (10 mL) over 30 minutes. BF3-Et2O (7.3 mmol, 2.7 eq.) was then added dropwise over 30 minutes. The solution was stirred at room temperature over night. 1N HCl was added dropwise to quench NaBH4 excess. The solvent was removed in vacuo, the residue dissolved in DCM, washed with water, brine. The organic layer was then dried over MgSO4 and the solvent removed in vacuo to give 425 mg of 3-fluoro 4-nitro benzyl alcohol (92% yield). The compound was used in the following step with no further purification.

Provenance & Evidence