Iodoethane → HCID 67280287, compound

HRID 1846010Notes

Reaction equation

HRID 1846010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].O.NN.[C:16]([O-])(=O)[CH3:17].[Na+].C(I)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:16][CH3:17])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24654Hydrazine hydrate (1:1)HCID 517045Sodium AcetateHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 67280287HCID 67280287, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 4-bromo-3-fluorobenzene-1-sulfonyl chloride (50 g, 0.184 mol) in THF (800 mL) at 0° C. was added hydrazine monohydrate (40-50%, 41.26 g, 0.644 mol) dropwise over 45 minutes. The reaction was stirred for 4 hours at room temperature and then the solvent was removed under reduced pressure to low volume. Heptane (100 mL) was added and the solid was filtered and washed several times with heptanes. The resulting solid was dissolved in ethanol (800 mL). Sodium acetate (90.56 g, 1.104 mol) and ethyl iodide (143.49 g, 0.92 mol) were added and the reaction heated to reflux for 18 hours. The reaction was allow to cool to room temperature, the solvent was removed under reduced pressure to 30% of the initial volume. The reaction mixture was diluted with water (500 mL) and extracted with CH2Cl2 (3×250 mL). The combined organic layers were washed with brine (2×300 mL), dried over Na2SO4, filtered and reduced to dryness to give a yellow oil. The crude was absorbed onto silica and purified (using siica gel column chromatography eluting with cyclohexane/EtOAc 8/2 to give the title compound as yellow solid in 64% yield, 31.70 g.

Workup

  1. customthe solvent was removed under reduced pressure to low volume
  2. additionHeptane (100 mL) was added
  3. filtrationthe solid was filtered
  4. washwashed several times with heptanes
  5. dissolutionThe resulting solid was dissolved in ethanol (800 mL)
  6. temperaturethe reaction heated
  7. temperatureto reflux for 18 hours
  8. temperatureto cool to room temperature
  9. customthe solvent was removed under reduced pressure to 30% of the initial volume
  10. additionThe reaction mixture was diluted with water (500 mL)
  11. extractionextracted with CH2Cl2 (3×250 mL)
  12. washThe combined organic layers were washed with brine (2×300 mL)
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customto give a yellow oil
  16. customThe crude was absorbed onto silica
  17. custompurified (
  18. washeluting with cyclohexane/EtOAc 8/2

Sources & evidence

ORD record
ord-310021c0df0442ddb5136d5e3804ed67
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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