Hydrochloric Acid → 5-Bromo-2-chloro-1,3-dimethoxybenzene

HRID 2300306Notes

Reaction equation

HRID 2300306 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[C:9](N)=[C:8]([O:15][CH3:16])[CH:7]=1.[ClH:17]>O>[Br:5][C:6]1[CH:12]=[C:11]([O:13][CH3:14])[C:9]([Cl:17])=[C:8]([O:15][CH3:16])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 3294234-Bromo-2,6-dimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 225579025-Bromo-2-chloro-1,3-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (97 mg) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (232 mg) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495 mg) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes, then at 100° C. for 2 hours, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water, dried over anhydrous sodium sulfate, and evaporated. The residue was subjected to a column of silica gel using hexane-ethyl acetate (10:1) as an eluent to give the title compound as white powder.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes
  2. waitat 100° C. for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-2a87873a3c60468bbd2a89f8971f093e
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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