Water → 5-Bromo-2,4-dimethoxybenzoic acid

HRID 1967446Notes

Reaction equation

HRID 1967446 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Br:14]Br.S([O-])([O-])=O.[Na+].[Na+].O>C(O)(=O)C>[Br:14][C:9]1[C:10]([O:12][CH3:13])=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 70522,4-Dimethoxybenzoic acidHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 135050975-Bromo-2,4-dimethoxybenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
25 °C

Procedure

2,4-Dimethoxybenzoic acid (30.0 g) was suspended in acetic acid (180 mL). A bromine (27.6 g)/acetic acid (60 mL) solution was slowly added dropwise to the suspension and, after completion of the dropwise addition, the mixture was stirred at 25° C. for 2 hrs, and the termination of the reaction was confirmed by HPLC. An aqueous solution of sodium sulfite (2.10 g) and water (360 mL) was added dropwise to the reaction mixture. After completion of the dropwise addition, the mixture was stirred at 25° C. for 1 hr. Precipitated crystals were collected by filtration, washed 4 times with water (150 mL), and vacuum dried to give 5-bromo-2,4-dimethoxybenzoic acid as white crystals (41.2 g, 96%).

Workup

  1. additionafter completion of the dropwise addition
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred at 25° C. for 1 hr
  4. customPrecipitated crystals
  5. filtrationwere collected by filtration
  6. washwashed 4 times with water (150 mL), and vacuum
  7. customdried

Sources & evidence

ORD record
ord-7e991debdf334bdd9ecf4dc31859eca3
Source dataset
uspto-grants-2013_04
Patent number
US08420821B2

Reaction notes

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