4-Bromo-3,5-dimethylphenol → 4-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

HRID 2170931Notes

Reaction equation

HRID 2170931 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].Cl[CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15]>CN1CCCC1=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[CH:4][C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 819704-Bromo-3,5-dimethylphenolHCID 5477654-Chloro-2-methylbutan-2-ol

Product 1

HCID 679729214-(4-Bromo-3,5-dimethylphenoxy)-2-methylbutan-2-ol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

10.0 g (49.7 mmol) 4-bromo-3,5-dimethylphenol and 10.3 g (74.6 mmol) K2OC3 are mixed with 20.0 mL N-methylpyrrolidone and heated to 100° C. 37.0 g (64.7 mmol) 4-chloro-2-methylbutan-2-ol (toluene solution from step 1) is added and the funnel is rinsed with 10.0 ml N-methylpyrrolidone. The reaction mixture is heated to 115° C. for approx. 3 h before 30.0 ml of the solvent is distilled off in vacuum. After full conversion the mixture is cooled to 20° C., 60.0 ml water is added and stirring is continued for 5 min. 90.0 ml n-heptane is added and the aqueous phase is separated. The organic phase is washed twice with 30.0 ml water. 20.0 ml solvent is distilled off and the mixture is cooled to 15° C. Seeds are added and stirring is continued for 1 h at 15° C. The suspension is cooled to −15° C. and stirred for 1 h. The product is filtered off, washed twice with cooled n-heptane and dried. Yield: 11.7 g; TLC: Rf=0.40 (silicagel, EtOAc:PE 2:8).

Workup

  1. washthe funnel is rinsed with 10.0 ml N-methylpyrrolidone
  2. temperatureThe reaction mixture is heated to 115° C. for approx. 3 h before 30.0 ml of the solvent
  3. distillationis distilled off in vacuum
  4. temperatureAfter full conversion the mixture is cooled to 20° C.
  5. addition60.0 ml water is added
  6. addition90.0 ml n-heptane is added
  7. customthe aqueous phase is separated
  8. washThe organic phase is washed twice with 30.0 ml water
  9. distillation20.0 ml solvent is distilled off
  10. temperaturethe mixture is cooled to 15° C
  11. additionSeeds are added
  12. stirringstirring
  13. waitis continued for 1 h at 15° C
  14. temperatureThe suspension is cooled to −15° C.
  15. stirringstirred for 1 h
  16. filtrationThe product is filtered off
  17. washwashed twice with cooled n-heptane
  18. customdried

Sources & evidence

ORD record
ord-75d888ab9c034e11892a20e98c608c2c
Source dataset
uspto-grants-2015_06
Patent number
US09051289B2

Reaction notes

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