Benzoyl Peroxide → (5-Bromomethyl-2-cyano-phenyl) acetate

HRID 8917Notes

Reaction equation

HRID 8917 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[C:12]#[N:13])(=[O:3])[CH3:2].[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[C:1]([O:4][C:5]1[CH:10]=[C:9]([CH2:11][Br:14])[CH:8]=[CH:7][C:6]=1[C:12]#[N:13])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 450912002-(Acetyloxy)-4-methylbenzonitrile

Product 1

HCID 68619125(5-Bromomethyl-2-cyano-phenyl) acetateYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of (2-cyano-5-methyl-phenyl) acetate (0.72 g, 4.11 mmol) in CCl4 (10 mL) was added recrystallized N-bromosuccinimide (0.767 g, 4.31 mmol) followed by benzoyl peroxide (56 mg, 0.23 mmol). The resultant mixture was heated to reflux for 2.5 hours then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (6:1 hexanes-EtOAc) provided 0.31 g (30%) of (5-bromomethyl-2-cyano-phenyl) acetate as a colorless oil. 1H NMR (CDCl3) δ 2.40 (s, 3H), 4.45 (s, 2H), 7.33 (s, 1H), 7.35 (d, 1H, J=9 Hz), 7.65 (d, 1H, J=9 Hz).

Workup

  1. temperatureto reflux for 2.5 hours
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (6:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-2ea7d7bfc1d74fbf8e0b93094079fe04
Source dataset
uspto-grants-2006_08
Patent number
US07091217B2

Reaction notes

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