Hydrogen Bromide → Methyl 5-bromo-2,4-dimethoxybenzoate

HRID 2293545Notes

Reaction equation

HRID 2293545 reaction equation
N[C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[BrH:16].N([O-])=O.[Na+]>CC(C)=O.O>[Br:16][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 16638096Methyl 5-amino-2,4-dimethoxybenzoateHCID 23668193Sodium Nitrite

Product 1

HCID 3859236Methyl 5-bromo-2,4-dimethoxybenzoate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A 0.65 g portion of methyl 5-amino-2,4-dimethoxybenzoate was dissolved in 10 ml of acetone and 1.5 ml of water, 1.80 ml of 48% hydrobromic acid was added, and then 0.23 g of sodium nitrite dissolved in 1 ml of water was added dropwise under ice-cooling, followed by a short period of stirring. Next, 0.51 g of cuprous bromide was added, and the mixture was warmed to room temperature. After completion of the reaction, insoluble matter was filtered, and the resulting residue was mixed with water, extracted with chloroform and then dried over anhydrous sodium sulfate. By evaporating the solvent under a reduced pressure, methyl 5-bromo-2,4-dimethoxybenzoate was obtained.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. waitfollowed by a short period
  4. customAfter completion of the reaction, insoluble matter
  5. filtrationwas filtered
  6. additionthe resulting residue was mixed with water
  7. extractionextracted with chloroform
  8. dry with materialdried over anhydrous sodium sulfate
  9. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-98040c4c3c804a10b5593217dcd00461
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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