Bromide ion → 3,5-Dibromo-2,4,6-trimethylphenol

HRID 1382481Notes

Reaction equation

HRID 1382481 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].BrBr.[BrH:13].[Br-:14]>C(Cl)(Cl)(Cl)Cl>[Br:13][C:7]1[C:2]([CH3:1])=[C:3]([OH:10])[C:4]([CH3:9])=[C:5]([Br:14])[C:6]=1[CH3:8]

Participants

6

Reactant 4

HCID 259Bromide ionHCID 260Hydrogen BromideHCID 106982,4,6-TrimethylphenolHCID 24408Bromine

Product 1

HCID 131086813,5-Dibromo-2,4,6-trimethylphenol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 136.2 gram portion of 2,4,6-trimethyl phenol (1 mole) is dissolved in 2 liters of carbon tetrachloride. Using a water bath for cooling, 230 ml of bromine (4.5 moles) is added at 20° C. to 26° C. over a period of 15 minutes. Hydrogen bromide gas is given off during the bromide addition, and a slurry of 3,5-dibromo-2,4,6-trimethylphenol is obtained. The temperature is increased to 70° C. to 75° C., and in the process, a solution is obtained. The solution is held at that temperature for 2 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 obtained is filtered and dried under a vacuum for 5 hours. A yield of 260 g is obtained, which analyzes by gas chromatography as 99% tribromomesitol.

Workup

  1. temperaturefor cooling

Sources & evidence

ORD record
ord-7dacd9d928a04319b73ea939424c6ef3
Source dataset
uspto-grants-1989_02
Patent number
US04806625

Reaction notes

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