Azobisisobutyronitrile → 1-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzene

HRID 1750867Notes

Reaction equation

HRID 1750867 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>ClC(Cl)C>[Br:22][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27754472-Methyl-5-nitrobenzotrifluoride

Product 1

HCID 468387611-(Bromomethyl)-4-nitro-2-(trifluoromethyl)benzeneYield 98.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

1-methyl-4-nitro-2-(trifluoromethyl)benzene (25 g, 122 mmol) was dissolved in dichloroethane (300 mL), followed by stirring. NBS (21.7 g, 122 mmol) and AIBN (2.0 g, 12.2 mmol) were added thereto, followed by further stirring for about 12 hours at 80° C. The resulting solid was filtered under reduced pressure, and dried with warm wind in an oven (40° C.) for 3 hours or more to obtain the title compound (34 g, 98%).

Workup

  1. stirringby further stirring for about 12 hours at 80° C
  2. filtrationThe resulting solid was filtered under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-3f352ea0510b4de4bc1cd7bf42ee0177
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

Loading…