Iodine → HCID 20086443, compound

Participants

Reaction Steps

A solution of 7-bromoisochroman (6.6 g; 30.98 mmmol) in THF (100 ml) was cooled to -78° C. and treated with 2.1 eq of tert-butyllithium (40 ml of a 1.7M solution). After stirring the dark red solution for one minute, iodine (8.64 g; 34.08 mmol) was added as a tetrahydrofuran (THF) solution (50 ml). The reaction mixture was stirred for 30 minutes at -78° C. and one hour at room temperature (about 24° C.). The reaction was quenched with saturated aqueous ammonium chloride, and the organic phase was washed with aqueous sodium thiosulfate and brine, dried, and freed of solvent. The crude product was recrystallized from hexane to provide the pure 5-iodoisochroman as a white crystalline solid, mp=54°-56° C. (4.1 g; 51%). 1H NMR (CDCl3): 2.79 (t, 2H); 3.94 (t,2H); 4.70 (s,2H); 6.85 (d, 1H); 7.32 (s, 1H); 7.46 (d, 1H). IR (nujol): 2931, 2852, 1550, 1252, 1190, 1105, 1005, 987 cm-1.

Provenance & Evidence