Phenol → HCID 10780965, compound

HRID 1106497Notes

Reaction equation

HRID 1106497 reaction equation
Br[C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([CH3:16])[CH:3]=1.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN1CCCC1=O.O>[O:23]([C:2]1[C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:16])[CH:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 10590825Methyl 4-bromo-5-methanesulfonyl-2-methylbenzoate

Product 1

HCID 10780965HCID 10780965, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2.5 g of methyl 4-bromo-5-methylsulfonyl-2-methylbenzoate, 0.94 g of phenol and 7.8 g of Cs2CO3 were dissolved in 40 ml of N-methylpyrrolidone and stirred at 160° C. for 4 h. The reaction mixture was poured onto 100 ml of a saturated aqueous NaHCO3 solution and 100 ml of water and extracted 5 times with 100 ml of EA each time. The aqueous phase was slowly adjusted to pH=2-3 using 6 N aqueous HCl solution and again extracted 5 times with 100 ml of EA each time. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. Chromatography on silica gel using DIP/2% HOAc yielded 1.85 g of a colorless solid,

Workup

  1. extractionextracted 5 times with 100 ml of EA each time
  2. extractionagain extracted 5 times with 100 ml of EA each time
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5fbb87bd95c448d2ac21d28d1577476a
Source dataset
uspto-grants-2000_05
Patent number
US06057322

Reaction notes

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