Bromine → HCID 67498507, compound

HRID 1183856Notes

Reaction equation

HRID 1183856 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[CH2:11][C:12]([O:14][CH3:15])=[O:13]>C(O)(=O)C>[Br:1][C:7]1[C:6]([CH3:10])=[C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:4]([CH3:3])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 58674897Methyl 2,6-dimethylbenzeneacetate

Product 1

HCID 67498507HCID 67498507, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
15 °C

Procedure

At about 15° C., a solution of 3.67 kg [23 mol] of bromine in 91 of glacial acetic acid is added dropwise to a solution of 3.175 kg [17.82 mol] of methyl 2,6-dimethylphenylacetate in 18 l of glacial acetic acid. The mixture is then stirred at 15° C. for another 2.5 hours, in order to warm to room temperature and stirred at room temperature for 48 hours. The reaction mixture is poured into 170 l of ice-water and extracted twice with in each case 60 l of methylene chloride. After removal of the solvent, 4 kg of a residue remain which, according to GC/MS, comprise 81.2% of methyl 3-bromo-2,6-dimethylphenylacetate (70.9% of theory),

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 48 hours
  3. extractionextracted twice with in each case 60 l of methylene chloride
  4. customAfter removal of the solvent, 4 kg of a residue

Sources & evidence

ORD record
ord-5862c1a7781448e486e2d9e7e0614d06
Source dataset
uspto-grants-2014_03
Patent number
US08664428B2

Reaction notes

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