N-bromobutanimide → 4-(bromomethyl)-3-(trifluoromethyl)benzonitrile

HRID 2384608Notes

Reaction equation

HRID 2384608 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27755984-Methyl-3-(trifluoromethyl)benzonitrile

Product 1

HCID 588271604-(bromomethyl)-3-(trifluoromethyl)benzonitrileYield 87.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methyl-3-trifluoromethyl-benzonitrile (370 mg, 2 mmol), N-Bromosuccinimide (356 mg, 2 mmol) and benzoyl peroxide (15 mg) in CCl4 (8 mL) was stirred at 85° C. for 16 hrs. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM. DCM layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid which was purified via flash chromatography (15% EtOAc in n-heptane) to yield the title compound as a solid (460 mg, 85%).

Workup

  1. customThe reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM
  2. dry with materialDCM layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo
  5. customto yield a crude solid which
  6. customwas purified via flash chromatography (15% EtOAc in n-heptane)

Sources & evidence

ORD record
ord-d9eec75fddde4bbf98ea026f38486c5f
Source dataset
uspto-grants-2012_09
Patent number
US08263781B2

Reaction notes

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