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

HRID 1039837Notes

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-26f8f7091e9848f0ade7da0d1cdc41d8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551978B2

Reaction notes

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