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

HRID 419560Notes

Reaction equation

HRID 419560 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.[O-:12][CH2:13][CH3:14].[Na+]>C(O)C.C(Cl)Cl>[CH2:13]([O:12][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[CH3:14]

Participants

5

Reactant 2

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

Product 1

HCID 155555014-Bromo-2-ethoxy-1-nitrobenzeneYield 99.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To 4-bromo-2-fluoro-1-nitrobenzene (8.2 g, 37.27 mmol) in 50 mL of ethanol was added 21% by weight sodium ethoxide (16.4 mL, 52.2 mmol). The mixture was stirred at 60° C. for 1 h. The EtOH was rotovaped down. The crude product was dissolved in DCM (100 mL), washed with H2O, dried (MgSO4), filtered, and rotovaped down to give the title compound of step A (9.14 g, 37.14 mmol, 99.7%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (d, J=8.61 Hz, 1H), 7.20 (d, J=1.83 Hz, 1H), 7.14 (dd, J=8.61, 1.83 Hz, 1H), 4.16 (q, J=7.02 Hz, 2H), 1.47 (t, J=6.96 Hz, 3H).

Workup

  1. washwashed with H2O
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-354cc62979d445d39ca5797ce6c39bc4
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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