6-tert-Butyl-m-cresol → 4-Bromo-2-(tert-butyl)-5-methylphenol

HRID 1003850

Reaction equation

HRID 1003850 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[Br:13]Br>C(Cl)(Cl)(Cl)Cl.O>[Br:13][C:9]1[C:8]([CH3:11])=[CH:7][C:6]([OH:12])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1

Participants

5

Reactant 2

HCID 69376-tert-Butyl-m-cresolHCID 24408Bromine

Product 1

HCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 2-t-butyl-5-methylphenol (24.6 g, 150 mmol) in CCl4 (100 mL) at 0° C. was added a solution of bromine (7.7 mL, 150 mmol) in CCl4 (100 mL) over a 4 hour period. The mixture was stirred at room temperature for 30 minutes and then diluted with H2O. The organic phase was separated, washed with saturated sodium bisulfite and brine, and dried (MgSO4). Concentration gave a residue which was chromatographed on silica gel, eluting with 6:1 hexanes:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.34 (s, 9 H), 2.24 (s, 3 H), 5.20 (s, 1 H), 6.54 (s, 1 H), 7.32 (s, 1 H).

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated sodium bisulfite and brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration
  5. customgave a residue which
  6. customwas chromatographed on silica gel
  7. washeluting with 6:1 hexanes

Sources & evidence

ORD record
ord-1a3a65a5ceb44aa089a1c793dbecdc8e
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Linked notes

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