2-Methylbenzoic acid → 4-Bromo-2-methylbenzoic acid

HRID 894169Notes

Reaction equation

HRID 894169 reaction equation
[Br:1]Br.[C:3]1([CH3:12])[C:4]([C:9]([OH:11])=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1>[Fe]>[Br:1][C:7]1[CH:8]=[C:3]([CH3:12])[C:4]([C:9]([OH:11])=[O:10])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 83732-Methylbenzoic acidHCID 24408Bromine

Product 1

HCID 995704-Bromo-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Chill a mixture of 140 gm. (0.875 mole) of bromine and 2.45 gm. of iron powder in an ice-bath and add portionwise during 15 minutes 93.31 gm. (0.7 mole) of o-toluic acid. Remove the reaction flask from the ice-bath and stir for 2 hours. Allow the resulting mushy solid to stand at room temperature overnight. Flush the reaction mixture with nitrogen. Finely grind the resulting solid cake, wash with water, aqueous sodium thiosulfate solution, water and dry to obtain the title compound together with the 3-bromo isomer (yield 144.7 gm., m.p. 112°-148° C.). The product is employed in the next step without further purification.

Workup

  1. temperatureChill
  2. additiona mixture of 140 gm
  3. customRemove the reaction flask from the ice-bath
  4. waitAllow the resulting mushy solid to stand at room temperature overnight
  5. customFlush the reaction mixture with nitrogen
  6. customFinely grind the resulting solid cake
  7. washwash with water, aqueous sodium thiosulfate solution, water
  8. customdry

Sources & evidence

ORD record
ord-606dc73dc45f4d448e4d7a46af196dc4
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

Loading…