Trifluoroacetic acid → 7-Chloro-3-hydroxy-3-(o-tolyl)indolin-2-one

Participants

Reaction Steps

In a 100 mL round-bottomed flask, a solution of 7-chloroindoline-2,3-dione (1 g, 5.51 mmol) in THF (10 mL) was cooled in an ice/water bath. A solution of o-tolylmagnesium bromide (2M, 5.51 mL, 11.01 mmol) was added, and the reaction mixture was removed from the cooling bath and warmed to room temperature. After 1 hour, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give Intermediate A-20A. MS (ES): m/z=272 [M−H−]; HPLC: RT=2.478 min (H2O/MeOH with TFA, CHROMOLITH® ODS S5 4.6×50 mm, gradient=4 min, wavelength=220 nm).

Provenance & Evidence