Sodium Hydroxide → 4-Bromo-2-ethylphenol

HRID 1453015Notes

Reaction equation

HRID 1453015 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 1N 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%). 1H NMR (CDCl3): δ 1.22 (t, 3H, J=7.5 Hz), 2.60 (q, 2H, J=7.5 Hz), 6.64 (d, 1H, J=8.5 Hz), 7.17 (dd, 1H, J=8.5, 2.5 Hz), 7.24 (d, 1H, J=2.5 Hz).

Workup

  1. custompartitioned between 1N 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-8e468e9ba6424a12897fd2912372ce1d
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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