Hydrochloric Acid → 3-Bromo-5-methoxybenzoic acid

HRID 588808Notes

Reaction equation

HRID 588808 reaction equation
N[C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([Br:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.N([O-])=O.[Na+].[PH2](O)=O>O.C1COCC1>[Br:13][C:8]1[CH:7]=[C:3]([CH:2]=[C:10]([O:11][CH3:12])[CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4124402Phosphinic AcidHCID 23668193Sodium NitriteHCID 454804572-Amino-5-bromo-3-methoxybenzoic acid

Product 1

HCID 40600483-Bromo-5-methoxybenzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-5-bromo-3-methoxybenzoic acid (4 g, 16.3 mmol) in water (20 mL) at 0° C., conc. HCl (7.5 mL, 90 mmol) and THF (20 mL) were added. The mixture was stirred for 30 min, and then NaNO2 (3.16 g, 45.8 mmol) was added. The resulting mixture was stirred for 2 h and then hypophosphorous acid (5.1 g, 76 mmol, 50% in H2O) was added to the reaction. The mixture was stirred at room temperature for 16 h. The precipitate was collected by filtration, washed with water and dried in vacuo to afford the desired product (3.2 g, 85% yield). ESI-MS m/z: 229.2 [M−H]−.

Workup

  1. stirringThe resulting mixture was stirred for 2 h
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-953a081f731f458c97a1236e914cf875
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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