Sodium Hydroxide → 2-Bromo-3-methyl-5-nitrobenzoic acid

HRID 723253Notes

Reaction equation

HRID 723253 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([CH3:13])[C:5]=1[Br:14].[OH-].[Na+]>C(O)C>[Br:14][C:5]1[C:6]([CH3:13])=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23433653Methyl 2-bromo-3-methyl-5-nitrobenzoate

Product 1

HCID 214691872-Bromo-3-methyl-5-nitrobenzoic acidYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-3-methyl-5-nitro-benzoic acid methyl ester ((Example 295: step d) 5.04 g) in ethanol (50 mL) was added a solution of aq NaOH (4M, 1.62 g, 40.5 mmol) and stirred at ambient temperature for 16 h. The resulting red colored solution was concentrated to dryness, dissolved in a minimum amount of H2O, and acidified with 1 N HCl to pH 3–4. The solid was filtered, washed with H2O (3×50 mL) dried under high vacuum to afford the title compound (4.5 g, 94% yield) as a pale yellow solid. 1H NMR (DMSO) δ 8.36–8.35 (m, 1H), 8.24–8.23 (m, 1H), 2.53 (s, 3H).

Workup

  1. concentrationThe resulting red colored solution was concentrated to dryness
  2. dissolutiondissolved in a minimum amount of H2O
  3. filtrationThe solid was filtered
  4. washwashed with H2O (3×50 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-47f099dd446d41c88dabd5c7b34f457a
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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