Citric Acid → 3-bromo-4-(bromomethyl)benzoic Acid

HRID 1873467Notes

Reaction equation

HRID 1873467 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][Br:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 116163143-bromo-4-(bromomethyl)benzoic AcidYield 43.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Bromo-4-methylbenzoic acid (10 g), N-bromosuccinimide (8.7 g) and 2,2′-azobisisobutyronitrile (0.4 g) were suspended in carbon tetrachloride (50 ml) and then heated to reflux for 2 hours. The mixture was returned to room temperature and added a 15% aqueous solution of citric acid (20 ml), and stirred for some time. Resulting crystals were filtered and washed with the 15% aqueous solution of citric acid (20 ml), and then dried, to obtain 3-bromo-4-(bromomethyl)benzoic acid (6 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customwas returned to room temperature
  4. customResulting crystals
  5. filtrationwere filtered
  6. washwashed with the 15% aqueous solution of citric acid (20 ml)
  7. customdried

Sources & evidence

ORD record
ord-4f415148a749447e94cd2cc20e55e462
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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