Sodium ethoxide → 4-Bromo-2-ethoxy-1-nitrobenzene

HRID 735661Notes

Reaction equation

HRID 735661 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][CH2:13][O-:14].[Na+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:14][CH2:13][CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 155555014-Bromo-2-ethoxy-1-nitrobenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (3 g, 13.6 mmol) and EtOH (50 mL) was added NaOEt (21% w/w, 50 mL). The mixture stirred for 2 h before concentrating in vacuo. The residue purified by flash chromatography (0-100% EtoAc/Hexane) to afford 62A (3 g, 90%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.49 (t, 3 H) 4.19 (q, 2 H) 7.22 (dd, 2 H) 7.71-7.81 (m, 1 H).

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue purified by flash chromatography (0-100% EtoAc/Hexane)

Sources & evidence

ORD record
ord-92c8ba3c220842eeaf79acc4c4af2946
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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