N-bromobutanimide → Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylate

HRID 2170619Notes

Reaction equation

HRID 2170619 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]2([C:10]([O:12][CH3:13])=[O:11])[CH2:9][CH2:8]2)=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 57443305Methyl 1-(p-tolyl)cyclopropanecarboxylate

Product 1

HCID 57443306Methyl 1-(4-(bromomethyl)phenyl)cyclopropanecarboxylateYield 97.7%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-(p-tolyl)cyclopropanecarboxylate (622 mg, 3.27 mmol) in carbon tetrachloride (16 mL) was added N-bromosuccinimide (611 mg) followed by benzoyl peroxide (40 mg). The resulting solution was heated at reflux overnight, and then diluted with methylene chloride. The mixture was washed with brine, dried on MgSO4, and concentrated to afford a colorless oil (860 mg, 97%).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux overnight
  3. washThe mixture was washed with brine
  4. customdried on MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1017ed48bbb74551815cae6c241a20de
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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