Sodium Hydroxide → 4-Bromo-2-chloro-6-ethylphenol

HRID 1453227Notes

Reaction equation

HRID 1453227 reaction equation
[OH-].[Na+].O.NN.[Br:6][C:7]1[CH:8]=[C:9]([Cl:17])[C:10]([OH:16])=[C:11]([C:13](=O)[CH3:14])[CH:12]=1>C(O)COCCOCCO>[Br:6][C:7]1[CH:12]=[C:11]([CH2:13][CH3:14])[C:10]([OH:16])=[C:9]([Cl:17])[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 242119391-(5-Bromo-3-chloro-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 587626844-Bromo-2-chloro-6-ethylphenolYield 83%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

Sodium hydroxide (1.2 g, 30 mmol) and hydrazine monohydrate (1.75 mL, 36 mmol) were added to a solution of 5′-bromo-3′-chloro-2′-hydroxyacetophenone (3 g, 12 mmol) dissolved in triethylene glycol (15 mL). The reaction mixture was heated to 160° C. for 72 hours 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 (2.34 g, 83%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.6 Hz, 3H), 2.65 (q, J=7.6 Hz, 2H), 5.55 (s, 1H), 7.17 (s, 1H), 7.31 (s, 1H).

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-5ba219b2df4d4a9d962d76e6c71051d4
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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