N-bromobutanimide → N-(4-bromo-2-(bromomethyl)phenyl)-2,2,2-trifluoroacetamide

HRID 17166Notes

Reaction equation

HRID 17166 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])=[C:4]([CH3:15])[CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([F:12])([F:13])[F:11])=[C:4]([CH2:15][Br:16])[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 789606N-(4-bromo-2-methylphenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 10992041N-(4-bromo-2-(bromomethyl)phenyl)-2,2,2-trifluoroacetamideYield 68%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of Example 478A (2.5 g, 8.9 mmol) and N-bromosuccinimide (1.58 g, 8.9 mmol) in carbon tetrachloride (25 mL) was irradiated with a 100-watt incandescent bulb overnight. The solution was filtered and the filtrate was concentrated. The concentrate was purified by flash chromatography on silica gel using 3-4% ethyl acetate/hexanes to give 2.17 g (68% yield) of the desired product. MS (ESI(−)) m/e 360, 362 (M−H)−.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe concentrate was purified by flash chromatography on silica gel using 3-4% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4797d2bbb4364b1292cb86e1745f47d2
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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