Bromine → 2-(3-broMo-2,6-diMethylphenyl)acetic acid

HRID 1183855Notes

Reaction equation

HRID 1183855 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]([OH:14])=[O:13]>C(O)(=O)C.C1CCCCC1>[Br:1][C:7]1[C:6]([CH3:10])=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[C:4]([CH3:3])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 198401152-(2,6-Dimethylphenyl)acetic acid

Product 1

HCID 529158182-(3-broMo-2,6-diMethylphenyl)acetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8078CyclohexaneSolvent

Conditions

Temperature
45 °C

Procedure

At 45° C., a solution of 8.5 kg [53.2 mol] of bromine in 10 l of glacial acetic acid is added dropwise to a solution of 6.86 kg [40.45 mol] of 2,6-dimethylphenylacetic acid in 401 of glacial acetic acid. The reaction mixture is then stirred at 45° C. for another 16 hours and concentrated on a rotary evaporator. The solid obtained is stirred in 10 l of cyclohexane at room temperature. After filtration, the residue is washed a little at a time with 10 l of cyclohexane and then dried. This gives 8.43 kg of a solid.

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. customThe solid obtained
  3. filtrationAfter filtration
  4. washthe residue is washed a little at a time with 10 l of cyclohexane
  5. customdried

Sources & evidence

ORD record
ord-0f0406bfc3ac4ddd96a3cb1240819e1f
Source dataset
uspto-grants-2014_03
Patent number
US08664428B2

Reaction notes

Loading…