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

HRID 1508896Notes

Reaction equation

HRID 1508896 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].C1C(=O)N([Br:22])C(=O)C1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([C:2]([CH3:1])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:13][CH:12]=1

Participants

5

Reactant 2

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

Product 1

HCID 18423131Methyl 2-(4-(bromomethyl)phenyl)-2-methylpropanoateYield 62.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A 500-mL round bottom flask, with stirrer bar, was charged with methyl 2-methyl-2-(p-tolyl)propanoate (2.50 g, 13.0 mmol), NBS (2.31 g, 13.0 mmol), and carbon tetrachloride (240 mL). The resulting solution was heated at reflux and AIBN (0.043 g, 0.26 mmol) was added. After stirring for 3.5 h, the reaction was cooled to room temperature and the solids removed by filtration. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica using hexane/ethyl acetate (100:0 to 80:20) as eluent as eluent to afford the title compound (2.20 g, 62%) as a colorless oil. MW=271.15. 1H NMR (CDCl3, 300 MHz) δ 7.39-7.28 (m, 4H), 4.48 (s, 2H), 3.65 (s, 3H), 1.57 (s, 6H).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux
  3. customthe solids removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica

Sources & evidence

ORD record
ord-94a6a672922d43ab934a3fdb81c2cd66
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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