N-bromobutanimide → Methyl 4-bromo-2-(bromomethyl)benzoate

HRID 2171094Notes

Reaction equation

HRID 2171094 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][Br:13])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22031226Methyl 4-bromo-2-methylbenzoate

Product 1

HCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoateYield 37.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of methyl 4-bromo-2-methylbenzoate (600 mg, 2.62 mmol) in carbon tetrachloride (70 mL) was added N-bromo succinimide (466 mg, 2.62 mmol) and benzoyl peroxide (12 mg) and the resultant reaction mixture was stirred in presence of sodium lamp at RT for 4 h. The reaction mixture was filtered through celite and washed with 2N sodium hydroxide solution, dried over sodium sulphate and concentrated under reduced pressure to afford Methyl 4-bromo-2-(bromomethyl)benzoate as a solid (300 mg, 37.5%).

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashed with 2N sodium hydroxide solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef1083564c8f4b8d9bee23548c9defd9
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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