N-bromobutanimide → Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoate

HRID 2261785Notes

Reaction equation

HRID 2261785 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]([CH3:13])([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)[CH3:5].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:14])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Br:15])=[CH:10][CH:11]=1)([CH3:5])[CH3:13]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13296592Methyl 2-methyl-2-(4-methylphenyl)propanoate

Product 1

HCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoateYield 72%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing solution of 2-Methyl-2-p-tolyl-propionic acid methyl ester (892 mg, 4.64 mmol) and N-bromosuccinimide (826 mg, 4.64 mmol) in CCl4 (120 mL) is added 2,2′-Azobisisobutyronitrile (12 mg, 0.073 mmol). After 5 h, the reaction is concentrated and the residue is chromatographed (SiO2 120 g, 5% to 20% EtOAc/Hex) to yield the title compound (906 mg, 72%) 1H NMR (400 MHz, CDCl3) δ 7.38-7.28 (m, 4H), 4.48 (s, 2H), 3.65 (s, 3H), 1.57 (s, 6H).

Workup

  1. concentrationthe reaction is concentrated
  2. customthe residue is chromatographed (SiO2 120 g, 5% to 20% EtOAc/Hex)

Sources & evidence

ORD record
ord-6566f4f144224c12bde757683bf3e3db
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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