Acetic Acid → 2-Bromobenzoic acid

HRID 364690Notes

Reaction equation

HRID 364690 reaction equation
[Br:1][C:2]1C=[CH:6][CH:5]=[CH:4][C:3]=1C.[C:9]([OH:12])(=[O:11])[CH3:10]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.[Br-].[Na+].C([O-])(=O)C.[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:10]=1[C:9]([OH:12])=[O:11]

Participants

7

Reactant 2

HCID 176Acetic AcidHCID 72362-Bromotoluene

Product 1

HCID 69402-Bromobenzoic acidYield 61.5%

Reagents, catalysts & solvents 4

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 253881Sodium BromideCatalystHCID 517045Sodium AcetateCatalystHCID 962WaterSolvent

Procedure

The test described in Example 1 was repeated using 300 g of o-bromotoluene, 660 g of acetic acid, 60 g of water, 6 g of cobalt acetate tetrahydrate, 5 g of sodium bromide and 5 g of sodium acetate. After a reaction time of 155 minutes, 217 g of o-bromobenzoic acid was obtained (61.6% of the theory).

Sources & evidence

ORD record
ord-3d9e9987f3244173a6577f37862ef46f
Source dataset
uspto-grants-1986_08
Patent number
US04605757

Reaction notes

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