1(3H)-Isobenzofuranone, 3-bromo- → HCID 69584846, compound

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Reaction Steps

A mixture of compound 108 (380 mg, 1.1 mmol), bromophthalide (213 mg, 1 mmol) and CsHCO3 (325 mg, 1 mmol) in acetone was stirred at room temperature for 16 h. After removing the solvent under reduced pressure, the residue was partitioned between 10% citric acid and ethyl acetate. The organic phase was separated and dried over MgSO4. After removing the solvent under reduced pressure, the resulting residue was treated with 50% trifluoroacetic acid in dichloromethane at room temperature for 30 min. After removing the solvent, the resulting residue was purified by reverse phase preparative HPLC to afford two separated stereoisomers 113 (123 mg) and 114 (120 mg), respectively. Compound 113: 1H NMR (CD3OD, 400 MHz): 1.43 (s, 3H), 2.98 (dd, 2H), 3.80 (s, 3H), 6.62–7.20 (m, 4H), 7.66–7.95 (m, 4H). MS (ESI) m/z 373.25 (M+H+) and Compound 114:1H NMR (CD3OD, 400 MHz): 1.44 (s, 3H), 2.99 (dd, 2H), 3.84 (s, 3H), 6.80–7.18 (m, 4H), 7.69–7.93 (m, 4H). MS (ESI) m/z 373.25 (M+H+).

Provenance & Evidence