Sodium Hydroxide → 1-Bromo-5-ethyl-4-methoxy-2-(phenylmethoxy)benzene

HRID 1453112Notes

Reaction equation

HRID 1453112 reaction equation
[OH-].[Na+].O.NN.[CH2:6]([O:13][C:14]1[C:19]([Br:20])=[CH:18][C:17]([C:21](=O)[CH3:22])=[C:16]([O:24][CH3:25])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)COCCOCCO>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([O:24][CH3:25])[C:17]([CH2:21][CH3:22])=[CH:18][C:19]=1[Br:20])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 58762417HCID 58762417, compound

Product 1

HCID 587623011-Bromo-5-ethyl-4-methoxy-2-(phenylmethoxy)benzeneYield 41.5%

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Conditions

Temperature
170 °C

Procedure

Sodium hydroxide (0.39 g, 9.7 mmol) and hydrazine monohydrate (0.57 mL, 11.7 mmol) were added to a solution of 1-(4-benzyloxy-5-bromo-2-methoxy-phenyl)-ethanone (1.3 g, 3.9 mmol) dissolved in triethylene glycol (5 mL). The reaction mixture was heated to 170° C. for 24 hours and then partitioned between 1N HCl and EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash silica gel chromatography (0% to 5% EtOAc in hexanes) to give the title compound (0.52 g, 40%). 1H NMR (400 MHz, CDCl3): δ 1.14 (t, J=7.3 Hz, 3H), 2.53 (q, J=7.3 Hz, 2H), 3.75 (s, 3H), 5.14 (s, 2H), 6.48 (s, 1H), 7.26 (s, 1H), 7.32 (m, 1H), 7.39 (m, 2H), 7.49 (d, J=8.3 Hz, 2H).

Workup

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

Sources & evidence

ORD record
ord-778f86b3c280484785fa51ba8a9dc4cf
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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