Benzyl Bromide → Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine

HRID 1097047Notes

Reaction equation

[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:11]([N:4]([CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=1)[C:3]1[CH:5]=[C:6]([CH3:10])[C:7]([I:9])=[CH:8][C:2]=1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2,5-dimethyl-4-iodoaniline (6.44 g, 26.1 mmol), benzyl bromide (11.50 g, 67.24 mmol) and potassium carbonate (8.20 g, 59.3 mmol) in EtOH (100 mL) was stirred at 50° C. for 12 h. The reaction mixture was then concentrated under reduced pressure. The residue (a purple solid) was mixed with DCM and this mixture was filtered using vacuum. The filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the title compound (9.35 g, 83% yield) as an oil.

Workup

concentrationThe reaction mixture was then concentrated under reduced pressure
additionThe residue (a purple solid) was mixed with DCM
filtrationthis mixture was filtered
customThe filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM)

Sources & evidence

ORD record: ord-e60f59831e024c798c90e146da067231
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138345B2

Reaction notes

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