Sodium Carbonate → HCID 18445418, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran (example 1f) (10 g, 44 mmol) was dissolved in glacial acetic acid (40 mL), iodine monochloride (10.86 g, 66.9 mmol) was added and the reaction mixture was heated at reflux for 72 hours then cooled to 0° C., and 1N NaOH was slowly added until pH=8 followed by Na2CO3 until the solution become colorless. The solution was extracted with ethyl acetate and the organic layer further washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (10% ethyl acetate in hexane) to give 8.7 g of 5-bromo-7-iodo-3,3-dimethyl-2,3-dihydro-benzofuran (56%). 1H NMR (300 MHz; CDCl3): 1.34 (s, 6H), 4.32 (s, 2H), 7.13 (d, J=2 Hz, 1H), 7.58 (d, J=2 Hz, 1H).

Provenance & Evidence