N-bromobutanimide → Methyl 2-(bromomethyl)benzoate

HRID 1886464Notes

Reaction equation

HRID 1886464 reaction equation
CC1C=CC=C(C)C=1C(O)=O.[CH3:12][C:13]1[CH:22]=[CH:21][CH:20]=[CH:19][C:14]=1[C:15]([O:17][CH3:18])=[O:16].[Br:23]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:18][O:17][C:15](=[O:16])[C:14]1[CH:19]=[CH:20][CH:21]=[CH:22][C:13]=1[CH2:12][Br:23]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 86746161HCID 86746161, compound

Product 1

HCID 2734813Methyl 2-(bromomethyl)benzoateYield 73%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.3 g (15.3 mmol) of methyl o-methylbenzoate (methyl o-toluate) in 20 mL of refluxing CCl4 was added 3 g of N-bromosuccinimide and 0.10 g AIBN. After 2.5 hours the mixture was cooled, diluted with 500 mL of CH2Cl2 and washed with 200 mL of H2O and 200 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was flash chromatographed with 5:1 hexane/ethyl acetate to yield the titled compound (2.56 g, 73%).

Workup

  1. temperatureAfter 2.5 hours the mixture was cooled
  2. washwashed with 200 mL of H2O and 200 mL of brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed with 5:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-c5aeb110b2fc41b58447cefc3a1f902f
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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