N-bromobutanimide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

HRID 225991Notes

Reaction equation

HRID 225991 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

Product 1

HCID 106781242-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzeneYield 44%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methyl-1-nitro-3-trifluoromethyl-benzene (5.0 g, 24.4 mmol) in CCl4 (300 mL) was added N-bromosuccinimide (4.35 g, 24.4 mmol) and benzoyl peroxide (0.11 g, 0.45 mmol). The mixture was heated to reflux and exposed to light (300 W) for 20 h. The mixture was cooled to room temperature, filtered and concentrated. Purification by column chromatography (EtOAc-hexanes) afforded 3.03 g (44%) of the benzyl bromide, a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.93 (s, 2 H), 7.63 (t, J=8.1 Hz, 1 H), 7.94 (d, J=7.8 Hz, 1 H), 8.06 (d, J=8.1 Hz, 1 H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (EtOAc-hexanes)

Sources & evidence

ORD record
ord-82a5997e89054bbc8d02b3cb53adfcc0
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

Loading…