2-(Benzyloxy)-5-fluorobenzaldehyde → (+/-)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one

Participants

Reaction Conditions

Reaction Steps

To the Grignard Solution A cooled to −78° C., a solution of 2-benzyloxy-5-fluoro-benzaldehyde (879 mg, 3.82 mmol, 1.0 eq.) in THF (10 mL) was added dropwise. The mixture was stirred at −78° C. for 1 hour and further at r.t. for 18 hours. The reaction was carefully quenched with 1M aq. NH4Cl soln. (50 mL) and AcOEt (100 mL) was added. The resulting suspension was filtered through celite and the filter cake was rinsed with water and AcOEt. The layers were separated and the aq. phase was extracted with AcOEt (2×150 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash master (column: 100 g, flow: 45 mL/min, Heptane to Heptane+45% AcOEt) to yield (±)-3-(2-benzyloxy-5-fluoro-phenyl)-3H-isobenzofuran-1-one as a white solid.

Provenance & Evidence