2,3,6-Trimethylphenol → 4-bromo-2,3,6-trimethyl-phenol

HRID 931848Notes

Reaction equation

HRID 931848 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[Br-:11].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.CO>[Br:11][C:6]1[CH:5]=[C:4]([CH3:9])[C:3]([OH:10])=[C:2]([CH3:1])[C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 170162,3,6-TrimethylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 108225484-bromo-2,3,6-trimethyl-phenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

10 g (71 mmol) of 2,3,6-trimethylphenol are initially introduced in a solvent mixture consisting of 250 ml of dichloromethane and 190 ml of methanol, and 35.4 g (72 mmol) of tetrabutylammonium tribromide in 170 ml of dichloromethane and 130 ml of methanol are added. After 5 h at room temperature, the batch is evaporated in a rotary evaporator, and the residue remaining is taken up in MTB. The organic solution is washed three times with water, dried over sodium sulfate and evaporated in a rotary evaporator. The crystalline residue obtained is employed in the next step without further work-up.

Workup

  1. additionare added
  2. customthe batch is evaporated in a rotary evaporator
  3. washThe organic solution is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in a rotary evaporator
  6. customThe crystalline residue obtained

Sources & evidence

ORD record
ord-129b732a4dfa4faebd04e3e20bcbb174
Source dataset
uspto-grants-2016_03
Patent number
US09296948B2

Reaction notes

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