Allyl bromide → N-allyl-N-[4-(perfluorohexyl)phenyl]-2,4-dinitrobenzenamine

HRID 50523Notes

Reaction equation

[F:1][C:2]([F:38])([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:27]=2[N+:35]([O-:37])=[O:36])=[CH:21][CH:20]=1)[C:3]([F:18])([F:17])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8].C(=O)([O-])[O-].[K+].[K+].[CH2:45](Br)[CH:46]=[CH2:47]>CN1C(=O)CCC1>[CH2:47]([N:25]([C:22]1[CH:23]=[CH:24][C:19]([C:2]([F:38])([F:1])[C:3]([F:18])([F:17])[C:4]([F:15])([F:16])[C:5]([F:13])([F:14])[C:6]([F:12])([F:11])[C:7]([F:10])([F:9])[F:8])=[CH:20][CH:21]=1)[C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][C:27]=1[N+:35]([O-:37])=[O:36])[CH:46]=[CH2:45]

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of N-[4-(perfluorohexyl)phenyl]-2,4-dinitrobenzenamine (3.6 g, 6.2 mmol), NMP (40 mL), potassium carbonate (3.0 g) and allyl bromide (0.65 mL) was stirred at 75° C. for 4 hr. The mixture was extracted in the normal fashion, and the product recrystallized to give N-allyl-N-[4-(perfluorohexyl)phenyl]-2,4-dinitrobenzenamine (2.9 g).

Workup

extractionThe mixture was extracted in the normal fashion
customthe product recrystallized

Sources & evidence

ORD record: ord-434ba6325e9d483294ed93a19cb9365f
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713135B2

Reaction notes

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