Sulfuric Acid → 5-Bromo-2-tert-butylphenol

HRID 1282315Notes

Reaction equation

HRID 1282315 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[CH3:9][C:10](O)([CH3:12])[CH3:11].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:10]([CH3:12])([CH3:11])[CH3:9])=[C:4]([OH:8])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 115633-BromophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 103313825-Bromo-2-tert-butylphenol

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 29.5 g (170.3 mmol) of 3-bromophenol in 100 mL of carbon tetrachloride (under a blanket of argon) was added 16.4 g (221.3 mmol) of 2-methyl-2-propanol followed by 20 mL of conc. sulfuric acid. The reaction mixture was allowed to stir at ambient temperature for 3.5 days. The clear, colorless solution turned pink and eventually turned purple in color. The reaction mixture was neutralized with sat. NaHCO3 (aq.) solution and then extracted between water and dichloromethane. The layers were separated and the aqueous phase was washed with dichloromethane. The organic phases were combined and washed with brine, dried over MgSO4, filtered and concentrated in vacua to a purple oil. Purification by flash chromatography (silica, 5% ethyl acetate in hexane) followed by kugelrohr distillation (85-95° C., 2mm Hg) gave the title compound as a clear, slightly yellow oil.

Workup

  1. extractionextracted between water and dichloromethane
  2. customThe layers were separated
  3. washthe aqueous phase was washed with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacua to a purple oil
  8. customPurification by flash chromatography (silica, 5% ethyl acetate in hexane)
  9. distillationfollowed by kugelrohr distillation (85-95° C., 2mm Hg)

Sources & evidence

ORD record
ord-ce955d1545e441c1950f49915877eb71
Source dataset
uspto-grants-2002_09
Patent number
US06455701B1

Reaction notes

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