2,6-Dimethylbenzoic acid → 3-bromo-2,6-dimethylbenzoic acid

HRID 1629729Notes

Reaction equation

HRID 1629729 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].CC([O-])=O.[Na+].[Br:17]Br>CC(O)=O>[Br:17][C:10]1[C:2]([CH3:1])=[C:3]([C:7]([CH3:11])=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 124392,6-Dimethylbenzoic acidHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 81671423-bromo-2,6-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2,6-dimethylbenzoic acid (25.00 g, 166 mmol) in HOAc (432 mL) was added NaOAc (16.39 g, 200 mmol) followed by bromine (11.2 mL, 216 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was poured onto ice water (800 mL) and stirred for 20 minutes. The solid was filtered off, washed with H2O and dried at 50° C. under vacuum to give INT 34.

Workup

  1. additionThe mixture was poured onto ice water (800 mL)
  2. stirringstirred for 20 minutes
  3. filtrationThe solid was filtered off
  4. washwashed with H2O
  5. customdried at 50° C. under vacuum
  6. customto give INT 34

Sources & evidence

ORD record
ord-b02aa4fa89644db8ab9ebddea7d86b58
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

Loading…