Benzoyl Peroxide → Ethyl 2-(5-bromomethyl-2-pyridinyl)benzoate

HRID 864455Notes

Reaction equation

HRID 864455 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1.C1C(=O)N([Br:26])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 19976479Ethyl 2-(5-methyl-2-pyridinyl)benzoate

Product 1

HCID 19976701Ethyl 2-(5-bromomethyl-2-pyridinyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Under nitrogen, the crude ethyl 2-(5-methyl-2-pyridinyl)benzoate from step 6 was treated with 1.7 g (9.5 mmol) of NBS and 160 mg (0.66 mmol) of benzoyl peroxide in 145 mL of anhydrous carbon tetrachloride at reflux for 2.5 h. The reaction was filtered under nitrogen and concentrated in vacuo to give crude ethyl 2-(5-bromomethyl-2-pyridinyl)benzoate; no purification was attempted.

Workup

  1. temperatureat reflux for 2.5 h
  2. filtrationThe reaction was filtered under nitrogen
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2886b4dc858c4a9c879e079be45a524f
Source dataset
uspto-grants-1996_10
Patent number
US05563139

Reaction notes

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