3-Methylbenzoic acid → 3-(Bromomethyl)benzoic acid

HRID 980461Notes

Reaction equation

HRID 980461 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 74183-Methylbenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 2456503-(Bromomethyl)benzoic acidYield 80.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

10 g (73.4 millimoles) of m-methyl-benzoic acid are dissolved in 75 ml of anhydrous carbon tetrachloride, whereupon 0.2 g of 2,2'-azo-bis-(2-methyl-propiontirile) and 13.72 g (77.07 millimoles) of N-bromo-succinimide are added. The reaction mixture is refluxed for 20 minutes, the formed succinimide is removed by filtering the warm mixture. The organic filtrate is washed with 15 ml of water, dried over sodium sulfate, filtered and the filtrate is evaporated in vacuo. The crude product thus obtained is recrystallized from a fivefold amount of carbon tetrachloride. Thus 12.71 g of the title compound are obtained, yield 80.5%.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is refluxed for 20 minutes
  3. customthe formed succinimide is removed
  4. filtrationby filtering the warm mixture
  5. washThe organic filtrate is washed with 15 ml of water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated in vacuo
  9. customThe crude product thus obtained
  10. customis recrystallized from a fivefold amount of carbon tetrachloride

Sources & evidence

ORD record
ord-d89322a071494439bfc9b357bb8f5b8f
Source dataset
uspto-grants-1987_01
Patent number
US04638002

Reaction notes

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