Trifluoromethanesulfonic anhydride → Ethyl 2-ethoxy-4'-fluoro-6-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-carboxylate

HRID 530976Notes

Reaction equation

HRID 530976 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH2:16]([O:18][C:19]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[C:21](O)[C:20]=1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[CH3:17]>N1C=CC=CC=1>[CH2:16]([O:18][C:19]1[CH:24]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:22]=[C:21]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])[C:20]=1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[CH3:17]

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 90423930Ethyl 2-ethoxy-4'-fluoro-6-hydroxybiphenyl-4-carboxylate

Product 1

HCID 117992433Ethyl 2-ethoxy-4'-fluoro-6-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (8.66 mL) was added at 0° C. to a mixture of ethyl 2-ethoxy-4′-fluoro-6-hydroxybiphenyl-4-carboxylate (13.0 g) and pyridine (80 mL), and the resultant mixture was stirred at the same temperature as above for 20 minutes. The reaction mixture was passed through a short silica gel (NH) column, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (15.6 g).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4b69b4ce59544614ade2e82a8299df26
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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