Water → HCID 59643014, compound

HRID 2251616Notes

Reaction equation

HRID 2251616 reaction equation
C[O:2][C:3]1[C:12]([O:13]C)=[CH:11][C:10]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6].O>CC(O)=O.Br.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[OH:2][C:3]1[C:12]([OH:13])=[CH:11][C:10]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

Participants

6

Reactant 2

HCID 962WaterHCID 59643020HCID 59643020, compound

Product 1

HCID 59643014HCID 59643014, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 2,3-dimethoxy-5-(toluene-4-sulfonyl)-benzoate (1.3 g, 4.036 mmol) was dissolved in 5 mL AcOH to which HBr (15 mL of a 33% solution in AcOH) and Bu4NBr (1.1 g, 3.4 mmol, 0.85 eq.) were added. The reaction mixture was stirred at 140° C. for 20 h, then H2O was slowly added and the mixture was extracted with EtOAc. The organic layer was washed twice with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc/AcOH 3:2:0.2→1:3:0.2) to yield the desired product as an orange solid.

Workup

  1. additionwere added
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed twice with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-34d6ed021965450dbabac7387b6e5f0f
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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