Benzoic acid, 4-hydroxy-3-nitro-, methyl ester → Methyl 3-bromo-4-hydroxy-5-nitrobenzoate

HRID 921612Notes

Reaction equation

HRID 921612 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C1C(=O)N([Br:22])C(=O)C1>C(O)(=O)C>[Br:22][C:11]1[CH:10]=[C:5]([CH:4]=[C:3]([N+:12]([O-:14])=[O:13])[C:2]=1[OH:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterHCID 67184N-bromobutanimide

Product 1

HCID 14985559Methyl 3-bromo-4-hydroxy-5-nitrobenzoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(I4A): Methyl 4-hydroxy-3-nitrobenzoate (15 g, 76 mmol) was suspended in acetic acid (152 ml) and then treated with NBS (20.31 g, 114 mmol). The mixture became a homogeneous yellow solution which was stirred for 2 h. The mixture was quenched with water and the suspension was filtered. Methyl 3-bromo-4-hydroxy-5-nitrobenzoate (20 g) was obtained as a yellow solid.

Workup

  1. customThe mixture was quenched with water
  2. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-0d65dac8ba0e44089f74eec7e92252da
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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