Hydrogen Bromide → Methyl 4-bromo-2,6-dichlorobenzoate

HRID 24712Notes

Reaction equation

HRID 24712 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7](N)=[CH:6][C:5]=1[Cl:12].N([O-])=O.[Na+].[BrH:18]>O.[Cu]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:18])=[CH:6][C:5]=1[Cl:12]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 23668193Sodium NitriteHCID 51341879Methyl 4-amino-2,6-dichlorobenzoate

Product 1

HCID 53951230Methyl 4-bromo-2,6-dichlorobenzoate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Amino-2,6-dichlorobenzoic acid methyl ester (1.00 g) was suspended in 40% aq. HBr and the mixture was cooled lto 0-5° C. After NaNO2 (376 mg) was added in small portions, the mixture was stirred for about 5 min. Copper (100 mg) was added and the mixture was warmed up to 100° C. The mixture was then stirred at 100° C. for 30 min, diluted with water and extracted with AcOEt. The extract was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 50:1) to give 4-bromo-2,6-dichlorobenzoic acid methyl ester (1.07 g).

Workup

  1. temperaturethe mixture was warmed up to 100° C
  2. stirringThe mixture was then stirred at 100° C. for 30 min
  3. extractionextracted with AcOEt
  4. dry with materialThe extract was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 50:1)

Sources & evidence

ORD record
ord-6af67051538744c08a07c1d4acd6976b
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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