Benzyl Bromide → Benzyl 2-methoxy-3-nitrobenzoate

HRID 2423237Notes

Reaction equation

HRID 2423237 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][O:16][C:17]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20]>CN(C=O)C>[CH3:15][O:16][C:17]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([O:21][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:20]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120151952-Methoxy-3-nitrobenzoic acid

Product 1

HCID 67246088Benzyl 2-methoxy-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, benzyl bromide (8.85 mL) and potassium carbonate (10.3 g) were added to a DMF (150 mL) solution of 2-methoxy-3-nitrobenzoic acid (9.80 g), followed by stirring for 70 minutes. The insoluble matter was separated by filtration, followed by evaporation under reduced pressure. This was subjected to liquid-liquid separation with ethyl acetate, aqueous sodium hydrogencarbonate solution, and hexane added thereto. The organic layer was washed with water and saturated brine in that order, dried, and then evaporated under reduced pressure to obtain benzyl 2-methoxy-3-nitrobenzoate (14.3 g).

Workup

  1. customThe insoluble matter was separated by filtration
  2. customfollowed by evaporation under reduced pressure
  3. customThis was subjected to liquid-liquid separation with ethyl acetate, aqueous sodium hydrogencarbonate solution, and hexane
  4. additionadded
  5. washThe organic layer was washed with water and saturated brine in that order
  6. customdried
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-75956b4746904735a1e1ff72c34da9c7
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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