Iodoethane → 6-Bromo-4-ethyl-2,2,7-trimethyl-4H-benzo[1,4]oxazin-3-one

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Reaction Steps

Compound 1B (1.0 g, 3.7 mmol) was dissolved in 25 mL of DMSO and added to a prestirred 2.0 M solution of potassium hydroxide (415 mg, 7.4 mmol) in DMSO. Next, ethyl iodide (0.6 mL, 7.4 mmol) was added and the reaction stirred at room temperature overnight. The reaction was quenched with 75 mL of water and extracted with dichloromethane. The combined organic extracts were dried over magnesium sulfate, filtered and excess solvent removed to yield 1.04 g (95%) of desired product. MS (electrospray): mass calculated for C13H16BrNO2, 297.04; m/z found 298, [M+H]+.

Provenance & Evidence