Sodium Methoxide → HCID 86723237, compound

HRID 1846011Notes

Reaction equation

HRID 1846011 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1F.[CH3:14][O-:15].[Na+]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH3:12])(=[O:10])=[O:9])=[CH:4][C:3]=1[O:15][CH3:14]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67280287HCID 67280287, compound

Product 1

HCID 86723237HCID 86723237, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed vessel 1-bromo-4-(ethylsulfonyl)-2-fluorobenzene (Preparation 19, 34.89 g, 0.131 mol) was dissolved in MeOH (400 mL) and sodium methoxide (35.3 g, 0.653 mol) was added. The reaction was heated at 100° C. for 12 hours and then allowed to cool to room temperature. The reaction mixture was diluted with water (750 mL) and the aqueous layer was extracted with CH2Cl2 (2×250 mL). The combined organic layers were washed with brine (300 mL), dried over Na2SO4, filtered and reduced to dryness to give a solid. The crude was purified by silica gel column chromatography eluting with cyclo-hexane/EtOAc gradient from 95/5 to 8/2 to afford the title compound as colourless solid in 75% yield, 27.32 g.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe aqueous layer was extracted with CH2Cl2 (2×250 mL)
  3. washThe combined organic layers were washed with brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customto give a solid
  7. customThe crude was purified by silica gel column chromatography
  8. washeluting with cyclo-hexane/EtOAc gradient from 95/5 to 8/2

Sources & evidence

ORD record
ord-516cad0843904ebfbf3833fd0912f92f
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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