Sodium Hydroxide → 4-Bromo-2-ethylphenol

HRID 858568Notes

Reaction equation

HRID 858568 reaction equation
[OH-].[Na+].O.NN.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([C:13](=O)[CH3:14])[CH:12]=1>C(O)COCCOCCO>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([OH:16])=[C:11]([CH2:13][CH3:14])[CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 959915'-Bromo-2'-hydroxyacetophenone

Product 1

HCID 878774-Bromo-2-ethylphenolYield 90%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

Sodium hydroxide (1.4 g, 35 mmol) and hydrazine monohydrate (2.04 mL, 42 mmol) were added to a solution of 5′-bromo-2′-hydroxyacetophenone (3 g, 14 mmol) dissolved in triethylene glycol (17 mL). The reaction mixture was heated to 170° C. for 24 h and then partitioned between 1 N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes) to give the title compound (2.52 g, 90%).

Workup

  1. custompartitioned between 1 N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash silica gel chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5ff9c930f24d4196b82d0bcef5b62032
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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