Isopropyl iodide → HCID 43140622, compound

Participants

Reaction Steps

Hydrazine hydrate (3.29 ml, 66.9 mmol) was added dropwise to a solution of 2-bromo-5-(chlorosulfonyl) benzoic acid (Preparation 22, 10.0 g, 33.4 mmol) in THF (100 mL) at 0° C. Once the addition was complete the mixture was allowed to warm to room temperature and the solid was collected by filtration. The solid was washed with heptane (3×20 mL) and dried under vacuum at 50° C. for 18 hours. The solid was dissolved in EtOH (100 mL) and NaOAc (16.4 g, 198 mmol) and 2-iodopropane (16.7 mL, 165 mmol) were added. The mixture was heated to reflux for 16 hours, cooled to room temperature and the solvent was evaporated under reduced pressure to leave an off-white solid. The solid was partitioned between EtOAc (50 mL) and 1M NaOH (100 mL). The aqueous layer was separated, acidified to pH=1 with 2M HCl and extracted with EtOAc (3×50 mL). The combined EtOAc extracts were dried over MgSO4 and the solvent was evaporated under reduced pressure to leave an orange oil. The oil was purified by silica gel column chromatography eluting with MeOH/CH2Cl2/AcOH 5:95.5:0.5 followed by a further chromatography eluting with heptanes/EtOAc 4:1 to give the title compound as a white solid 8% yield, 0.78 g.

Provenance & Evidence