Hydrochloric Acid → Methyl 5-bromo-2-chloro-3-methoxybenzoate

HRID 576328Notes

Reaction equation

HRID 576328 reaction equation
N[C:2]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([Br:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[ClH:15].N([O-])=O.[Na+]>O>[Br:14][C:9]1[CH:10]=[C:11]([O:12][CH3:13])[C:2]([Cl:15])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 58801718Methyl 5-bromo-2-chloro-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of compound 54 (27.0 g, 103 mmol) in H2O (70 mL) and conc.HCl (70 mL) was added dropwise a solution of NaNO2 (21.5 g, 311 mmol) in H2O (50 mL) at 0° C. After being stirred for 1 hour, a solution of Cu(I)Cl in conc.HCl (80 mL) was added to the reaction mixture dropwise at 0° C. The mixture was stirred at room temperature for 18 hours. To the mixture was added water (300 mL) and extracted with EtOAc (500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product 55 was dried under high vacuum and used without further purification (29.0 g, 100%) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with EtOAc (500 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dry with materialThe crude product 55 was dried under high vacuum
  7. customused without further purification (29.0 g, 100%) as a white solid

Sources & evidence

ORD record
ord-619e1517e6714435a26d3efafd93cea2
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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