N-bromobutanimide → 1227587-81-6

HRID 1946336Notes

Reaction equation

HRID 1946336 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C1C(=O)N([Br:22])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 106558302-Methyl-4-nitrobenzotrifluoride

Product 1

HCID 667707571227587-81-6Yield 104.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-methyl-4-nitrobenzotrifluoride (5.05 g, 24.6 mmol, synthesised according to Journal of medicinal chemistry (1996), 39(23), 4608-4621) in carbon tetrachloride (50 ml) was added NBS (4.77 g, 26.8 mmol, Aldrich) and then benzoyl peroxide (0.110 g, 0.454 mmol, Acros). The mixture was heated to 90° C. overnight, cooled to ambient temperature and the allowed to stand for 4 days. The suspension was filtered and the residue washed with carbon tetrachloride (10 ml). The solvent was removed in vacuo to give 2-(bromomethyl)-4-nitro-1-(trifluoromethyl)benzene as a mobile orange oil (7.33 g).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe suspension was filtered
  3. washthe residue washed with carbon tetrachloride (10 ml)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7c35c873e0cb4bfcaa176736f78eb611
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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