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Azobisisobutyronitrile → 1-(Bromomethyl)-2-iodo-3-nitro-5-(trifluoromethyl)benzene

HRID 2093181
Notes
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Reaction equation

HRID 2093181 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[I:15].C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[I:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 57704804HCID 57704804, compound

Product 1

HCID 577048561-(Bromomethyl)-2-iodo-3-nitro-5-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of the title compound from Step C (0.38 g, 1.15 mmol), NBS (0.24 g, 1.38 mmol) and catalytic amount of AIBN in carbon tetrachloride (5 ml) was heated to reflux for 3 days. During the period more AIBN was added daily. The mixture was cooled and concentrated. The title compound was obtained after flash column using hexane as the eluant. 1H NMR (CDCl3, 500 MHz): δ 7.91 (s, 1H), 7.80 (s, 1H), 4.75 (s, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-025265677ad142828cfccc0eb2228fdd
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08440702B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes