Allyl bromide → Methyl 3-allyloxy-4-nitro-benzoate

HRID 2217367

Reaction equation

HRID 2217367 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23]>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH2:23][CH:22]=[CH2:21])[CH:5]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 59768302Methyl 3-allyloxy-4-nitro-benzoateYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-hydroxy-4-nitro-benzoic acid methyl ester (50.0 g, 253.6 mmol) in acetone (1 L) was added potassium carbonate (105.0 gram, 759.7 mmol) and allyl bromide (44.0 mL, 508.4 mmol). The reaction mixture was heated to reflux overnight and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give 3-allyloxy-4-nitro-benzoic acid methyl ester as solid (59.4 g, 98.8%). 1H NMR (CDCl3) δ 3.96 (s, 3H), 4.75 (dt, 2H, J=5.0 Hz, 1.6 Hz), 5.36 (ddt, 1H, J=10.6 Hz, 1.4 Hz, 1.4 Hz), 5.50 (ddt, 1H, J=17.2 Hz, 1.6 Hz, 1.6 Hz), 6.05 (ddt, 1H, J=17.3 Hz, 10.6 Hz, 5.0 Hz), 7.69 (dd, 1H, J=8.33 Hz, 1.58 Hz), 7.75 (d, 1H, J=1.55 Hz), 7.83 (d, 1H, J=8.34 Hz).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customthe insoluble material was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-979b4f4e7b23452b93e5eacb2b08d0a2
Source dataset
uspto-grants-2008_08
Patent number
US07407980B2

Linked notes

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