1,4-Dioxane → HCID 86723247, compound

HRID 1846024Notes

Reaction equation

HRID 1846024 reaction equation
O1[CH2:6][CH2:5][O:4][CH2:3]C1.CC(C)([O-])C.[K+].[Br:13][C:14]1C=C[C:17]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[CH:16][C:15]=1F>CO>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH:23]([CH3:25])[CH3:24])(=[O:21])=[O:22])=[CH:6][C:5]=1[O:4][CH3:3]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 23665647Potassium tert-butoxideHCID 86723246HCID 86723246, compound

Product 1

HCID 86723247HCID 86723247, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To dioxane (5 mL) and MeOH (0.216 mL) was added a solution of potassium tert-butoxide (1M in THF, 5.16 mL) and the mixture stirred for 15 minutes. To the mixture was added 1-bromo-2-fluoro-4-(isopropylsulfonyl)benzene (Preparation 34, 500 mg, 1.78 mmol) and the reaction mixture stirred for 16 hours at 60° C. The cooled reaction mixture was quenched with water (15 mL), and extracted with EtOAc (3×15 mL). The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. The crude material was purified by silica gel column chromatography eluting with EtOAc/heptanes 33/67-100/0 to afford title compound as a colourless solid in 75% yield.

Workup

  1. stirringthe reaction mixture stirred for 16 hours at 60° C
  2. customThe cooled reaction mixture
  3. customwas quenched with water (15 mL)
  4. extractionextracted with EtOAc (3×15 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe crude material was purified by silica gel column chromatography
  9. washeluting with EtOAc/heptanes 33/67-100/0

Sources & evidence

ORD record
ord-0eb1d136aa894e69be527211b6d41b80
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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