N-bromobutanimide → 2-(4-Bromomethyl-phenyl)-2-methyl-propionic acid ethyl ester

HRID 23790

Reaction equation

HRID 23790 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH3:14])([C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.O.C(Cl)Cl.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][Br:16])=[CH:11][CH:12]=1)([CH3:14])[CH3:6])[CH3:2]

Participants

7

Reactant 2

HCID 67184N-bromobutanimideHCID 583752Ethyl 2-methyl-2-(4-methylphenyl)propanoate

Product 1

HCID 154287362-(4-Bromomethyl-phenyl)-2-methyl-propionic acid ethyl esterYield 97.7%

Reagents, catalysts & solvents 4

HCID 749781,1'-Azobis(cyclohexanecarbonitrile)CatalystHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-p-tolyl-propionic acid ethyl ester (263 mg, 1.27 mmol) and N-bromosuccinimide (272 mg, 1.53 mmol) in CCl4 (15 mL) was added 1,1′-azobis(cyclohexanecarbonitrile) (15.5 mg, 0.06 mmol). The reaction was heated at reflux for 1 h and was diluted with water and CH2Cl2. The layers were separated and the aqueous layer was washed with CH2Cl2 (3×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Medium pressure chromatography (95:5 hexanes:EtOAc) provided 2-(4-bromomethyl-phenyl)-2-methyl-propionic acid ethyl ester (354 mg). 1H NMR (400 MHz, CDCl3) δ 7.31 (m, 4H), 4.47 (s, 2H), 4.10 (q, 2H), 1.54 (s, 6H), 1.17 (t, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. customThe layers were separated
  4. washthe aqueous layer was washed with CH2Cl2 (3×)
  5. dry with materialThe combined organic solutions were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd1633bcc9154411932189915768a2b7
Source dataset
uspto-grants-2005_02
Patent number
US06852863B2

Linked notes

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