4-Iodoaniline → HCID 67059804, compound

Participants

Reaction Conditions

Reaction Steps

Citronellylmagnesium bromide [from S-citronellylbromide (14.46 g, 66 mmol) and magnesium (3.20 g, 132 mmol)] in THF (80 mL) was added to a suspension of 4-iodoaniline (4.38 g, 20 mmol) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II) (PdCl2(dppf), 0.150 g, 0.2 mmol) in THF (25 mL) maintained at −78° C. under a nitrogen atmosphere. After stirring for 10 minutes at −78° C., the reaction mixture was heated under reflux for 16 hours and then quenched with 5% hydrochloric acid (HCl). The aqueous solution was then extracted with ether (3×30 mL) and the combined fractions were washed with water, dried over magnesium sulfate (MgSO4), and the solvent was evaporated to give 4-[(3S)-3,7-dimethyl-6-octenyl]aniline as a dark oil (41.9 g) which was used in the next step without additional purification.

Provenance & Evidence