4-Iodoaniline → HCID 67059804, compound

HRID 601446Notes

Reaction equation

[CH2:1]([Mg]Br)[CH2:2][CH:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH3:4].I[C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>C1COCC1.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:4][C@@H:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])[CH2:2][CH2:1][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

temperaturethe reaction mixture was heated
temperatureunder reflux for 16 hours
customquenched with 5% hydrochloric acid (HCl)
extractionThe aqueous solution was then extracted with ether (3×30 mL)
washthe combined fractions were washed with water
dry with materialdried over magnesium sulfate (MgSO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-2009b25dc41743a3b632daecf2fef8ae
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902363B2

Reaction notes

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