tert-Butanol → 1-(4-Fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanol

HRID 741684Notes

Reaction equation

HRID 741684 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13](SC)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:19]C(O)(C)C.O[O:25][S:26]([O-:28])=O.[K+]>C(Cl)Cl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:18])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([S:26]([CH3:19])(=[O:28])=[O:25])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 194267921-(4-Fluorophenyl)-2-(4-(methylthio)phenyl)ethanolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 194267951-(4-Fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of the product of step 1 (42 g, 160 mmol) in a mixture of CH2Cl2 (200 mL), t-BuOH (500 mL) was added a suspension of oxone (144 g, 234 mmol) in 1 L of H2O. The mixture was stirred for 72 h. CH2Cl2 was added until all solid dissolved. The resulting mixture was extracted with EtOAc. The organic extracts were dried (Na2SO4) and concentrated to give 47 g of the title compound.

Workup

  1. additionwas added
  2. dissolutiondissolved
  3. extractionThe resulting mixture was extracted with EtOAc
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb8ba6c4bdaf417590451d616c8a1520
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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