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

HRID 460368Notes

Reaction equation

HRID 460368 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-dimethoxybenzeneYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium nitrite (97.0 mg, 1.40 mmol) in water (2.0 mL) was added dropwise to an ice-cold suspension of 4-bromo-2,6-dimethoxyaniline (Z. Naturforsch., B24(5), 524–527 (1969)) (232.0 mg, 1.00 mmol) in 6.0 M hydrochloric acid (2.5 mL). After stirring in ice for 30 minutes, a solution of cupric chloride (495.0 mg, 5.00 mmol) in concentrated hydrochloric acid (2.0 mL) was added. The reaction mixture was stirred at room temperature for 30 minutes and 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 concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-bromo-4-chloro-3,5-dimethoxybenzene as a colorless amorphous powder (230.0 mg, yield: 92%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 30 minutes and at 100° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dad8d9854ba84a2893fc35baf51bb3fb
Source dataset
uspto-grants-2007_03
Patent number
US07196101B2

Reaction notes

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