3,5-Dibromo-2,4,6-trimethylphenol → 3,5-Dibromo-4-(bromomethyl)-2,6-dimethylphenol

HRID 649695Notes

Reaction equation

HRID 649695 reaction equation
[Br:1]C(Br)(Br)C1C=C(C)C(O)=C(C)C=1.[Br:14][C:15]1[C:20]([CH3:21])=[C:19]([OH:22])[C:18]([CH3:23])=[C:17]([Br:24])[C:16]=1[CH3:25]>>[Br:1][CH2:25][C:16]1[C:15]([Br:14])=[C:20]([CH3:21])[C:19]([OH:22])=[C:18]([CH3:23])[C:17]=1[Br:24]

Participants

3

Reactant 2

HCID 131086813,5-Dibromo-2,4,6-trimethylphenolHCID 131715226Tribromomesitol

Product 1

HCID 139546603,5-Dibromo-4-(bromomethyl)-2,6-dimethylphenol

Conditions

Temperature
25 °C

Procedure

The temperature is increased to 70° C.-75° C., and a solution is obtained. The solution is held at 70° C.-75° C. for 3 hours. The unreacted bromine is removed by distillation with the aid of 1 liter of carbon tetrachloride. When 1 liter of solvent remains with the product, the solution is cooled to 25° C. The light brown solid which is obtained is filtered and is dried under vacuum for 5 hours. A yield of 250 g (67 percent) is obtained, which analysis by gas chromatography shows to be 97 percent tribromomesitol and 3 percent dibromomesitol. The product has a melting point of 144° C.-146° C. and has the following proton nuclear magnetic resonance spectrum (CDCl3), δ: 2.30 (s, 6H), 4.90 (s, 2H), which is consistent with the structure of the product.

Workup

  1. temperatureThe temperature is increased to 70° C.-75° C.
  2. customa solution is obtained
  3. customThe unreacted bromine is removed by distillation with the aid of 1 liter of carbon tetrachloride
  4. customThe light brown solid which is obtained
  5. filtrationis filtered
  6. customis dried under vacuum for 5 hours
  7. customA yield of 250 g (67 percent) is obtained

Sources & evidence

ORD record
ord-7d8ba5a8cd434238914e11812ca8f44f
Source dataset
uspto-grants-1988_04
Patent number
US04740636

Reaction notes

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