Pyridine → Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

HRID 1096950Notes

Reaction equation

HRID 1096950 reaction equation
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:24]=[C:25]([C:35]([O:37][CH3:38])=[O:36])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[F:7][C:8]([F:21])([F:20])[S:9]([O:12][C:23]1[CH:24]=[C:25]([C:35]([O:37][CH3:38])=[O:36])[CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:28]=1)(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 67749Trifluoromethanesulfonic anhydrideHCID 18945322Methyl 3-hydroxy-5-phenylbenzoate

Product 1

HCID 57930914Methyl 5-{[(trifluoromethyl)sulfonyl]oxy}biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

With cooling with ice, pyridine (1.2 mL) and trifluoromethanesulfonic acid anhydride (1.2 mL) were added to a CHCl3 (40 mL) solution of methyl 5-hydroxybiphenyl-3-carboxylate, and stirred for 30 minutes with cooling with ice. Aqueous ammonium chloride was added to the reaction liquid, extracted with ethyl acetate, and the organic layer was washed with water, aqueous saturated sodium bicarbonate solution and saturated saline water. This was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound as a yellow oil. Not purified, this was used in the next step.

Workup

  1. temperaturewith cooling with ice
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water, aqueous saturated sodium bicarbonate solution and saturated saline water
  4. dry with materialThis was dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c681af8e231949be8797ae88eb495444
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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