Sodium Methoxide → 4-Chloro-2-(methoxymethyl)-1-nitrobenzene

HRID 1918397Notes

Reaction equation

HRID 1918397 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7]Br.[CH3:13][O-:14].[Na+]>CO>[N+:10]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH2:7][O:14][CH3:13])([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 124231272-(Bromomethyl)-4-chloro-1-nitrobenzene

Product 1

HCID 133378004-Chloro-2-(methoxymethyl)-1-nitrobenzeneYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2.15 g of 5-chloro-2-nitrobenzylbromide is dissolved in approximately 25 ml methanol at room temperature. 1.86 g of 25% sodium methoxide in methanol is added and stirring continued for 0° C. 1 hour after which 10 wt % additional sodium methoxide is added to complete the conversion. The solvent is evaporated and the residue is dissolved in 100 ml dichloromethane and washed with 25 ml water (2X). Evaporation provided 1.6 g of 4-nitro-3-methoxymethylchlorobenzene. 1H-NMR (500 MHz, CDC13) δ (ppm) 3.527 (s, 3H), 4.838 (s, 2H), 7.399-7.416 (dd, 1H), 7.824-7.826 (d, 1H), 8.066-8.084 (d, 1H).

Workup

  1. customcontinued for 0° C
  2. customThe solvent is evaporated
  3. dissolutionthe residue is dissolved in 100 ml dichloromethane
  4. washwashed with 25 ml water (2X)
  5. customEvaporation

Sources & evidence

ORD record
ord-942e341242de433d86cecc1a66ea36a9
Source dataset
uspto-grants-2013_12
Patent number
US08618326B2

Reaction notes

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