Chloride → HCID 86757893, compound

HRID 277688Notes

Reaction equation

HRID 277688 reaction equation
[OH-].[K+].[F:3][C:4]([F:15])([F:14])[CH:5]([F:13])[C:6]([F:12])([F:11])[S:7]([O-:10])(=[O:9])=[O:8].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([IH+:23])=[CH:19][CH:18]=1.[OH:24][C:25]1[CH:30]=[CH:29][C:28]([IH+])=[CH:27][CH:26]=1.F[C:33](F)(F)[CH:34](F)[C:35](F)(F)S([O-])(=O)=O.[Cl-].[C:46](Br)([CH3:49])([CH3:48])[CH3:47]>C(O)C.C(OCC)C>[F:15][C:4]([F:3])([F:14])[CH:5]([F:13])[C:6]([F:11])([F:12])[S:7]([O-:10])(=[O:8])=[O:9].[C:34]([O:16][C:17]1[CH:22]=[CH:21][C:20]([I+:23][C:28]2[CH:29]=[CH:30][C:25]([O:24][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:26][CH:27]=2)=[CH:19][CH:18]=1)([CH3:35])([CH3:4])[CH3:33]

Participants

7

Reactant 4

HCID 312ChlorideHCID 10485t-Butyl bromideHCID 14797Potassium HydroxideHCID 86757894HCID 86757894, compound

Product 1

HCID 86757893HCID 86757893, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

6.2 g (0.11 mol) of potassium hydroxide was dissolved in 250 ml of ethanol. 27.2 g (0.05 mol) of bis-(4-hydroxyphenyliodonium) 3,3,3,2,1,1-hexafluoropropane sulfonate (prepared from a metathesis reaction of chloride) was added to the solution. The mixture was stirred for 3 hours. The solution was then heated to 50° C., and 15.1 g (0.11 mol) of t-butyl bromide was added dropwise thereto. The mixture was heated under reflux for 6 hours. The precipitates were removed by filtration. The solvent was removed from the filtrate by distillation. The residue was dissolved in 250 ml of ethyl acetate. The solution was washed several times with water, and then dried. The solvent was removed to obtain a yellow oil. The contemplated material was obtained by recrystallization from diethyl ether. The structure was confirmed by 1H-NMR (CDCl3): δ=1.43 (s, 18H), 5.00-5.30 (d[m], 1H), 7.17-7.21 (d, 4H), 7.55-7.59 ppm (d, 4H).

Workup

  1. additionwas added to the solution
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 6 hours
  4. customThe precipitates were removed by filtration
  5. customThe solvent was removed from the filtrate by distillation
  6. dissolutionThe residue was dissolved in 250 ml of ethyl acetate
  7. washThe solution was washed several times with water
  8. customdried
  9. customThe solvent was removed
  10. customto obtain a yellow oil

Sources & evidence

ORD record
ord-a27af7f619e54ed493fa0f2284618393
Source dataset
uspto-grants-2002_03
Patent number
US06358665B1

Reaction notes

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