Bromoacetic Acid → 2,4-Dimethoxy-5-methylsulfonylbenzoic acid

HRID 2293551Notes

Reaction equation

HRID 2293551 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[C:7](=O)(O)[O-].[Na+].Cl[S:13]([C:16]1[C:17]([O:27][CH3:28])=[CH:18][C:19]([O:25][CH3:26])=[C:20]([CH:24]=1)[C:21]([OH:23])=[O:22])(=[O:15])=[O:14].BrCC(O)=O>O>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([O:27][CH3:28])[C:16]([S:13]([CH3:7])(=[O:15])=[O:14])=[CH:24][C:20]=1[C:21]([OH:23])=[O:22]

Participants

6

Reactant 4

HCID 6227Bromoacetic AcidHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 167713625-Chlorosulfonyl-2,4-dimethoxybenzoic acid

Product 1

HCID 214770622,4-Dimethoxy-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 0.90 g portion of sodium sulfite and 1.81 g of sodium bicarbonate were dissolved in 6 ml of water, and 2.00 g of 5-chlorosulfonyl-2,4-dimethoxybenzoic acid was added thereto, followed by 1 hour stirring. Next, 1.50 g of bromoacetic acid was added, followed by stirring at 75° C. After completion of the reaction, the reaction solution was poured into cool water, and the thus precipitated product of interest was collected by filtration, washed with water and then dried under a reduced pressure to give 2,4-dimethoxy-5-methylsulfonylbenzoic acid, which was used in the next reaction without purification.

Workup

  1. stirringby stirring at 75° C
  2. customAfter completion of the reaction
  3. additionthe reaction solution was poured
  4. filtrationthe thus precipitated product of interest was collected by filtration
  5. washwashed with water
  6. customdried under a reduced pressure

Sources & evidence

ORD record
ord-584db219145d4c6c920f33dc83de69bd
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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