Benzyl Alcohol → Benzyl 4-fluorobenzoate

Participants

Reaction Steps

A mixture of 4-fluorobenzoic acid (1.0 g, 7.13 mmol) in Et2O was treated with oxallyl chloride (760 mL, 8.55 mmol) and a catalytic amount of DMF. The mixture was then stirred until the evolution of gas stopped. The mixture was then filtered and concentrated under reduced pressure. The residue was dissolved in a small volume of CH2Cl2 and the solution was added in a drop wise manner to a mixture of benzyl alcohol (770 mg, 7.13 mmol), diisopropyl ethyl amine (2.49 mL, 14.3 mmol) and a catalytic amount of DMAP in CH2Cl2 (20 mL). After stirring overnight the reaction mixture was concentrated and the residue was passed through a silica gel plug with 10% Et2O in hexanes to afford the product (991 mg, Yield: 60%). FIRMS m/z calcd for C14H11O2F [M+H]+: 230.0743. Found: 230.0742.

Provenance & Evidence