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

HRID 1504914Notes

Reaction equation

HRID 1504914 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 (2×). Evaporation provided 1.6 g of 4-nitro-3-methoxymethylchlorobenzene. 1H-NMR (500 MHz, CDCl3) 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 (2×)
  5. customEvaporation

Sources & evidence

ORD record
ord-f392b436170047a5bc483277a5ca5a65
Source dataset
uspto-grants-2015_12
Patent number
US09216945B2

Reaction notes

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