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

HRID 531010Notes

Reaction equation

HRID 531010 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH2:30][CH2:31][CH3:32])=[CH:27][C:26]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:25][C:24]=2O)=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:24]([O:6][S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[CH:25][C:26]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:27][C:28]=2[O:29][CH2:30][CH2:31][CH3:32])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 90424026Ethyl 4'-fluoro-2-hydroxy-6-propoxybiphenyl-4-carboxylate

Product 1

HCID 117992413Ethyl 4'-fluoro-2-propoxy-6-(((trifluoromethyl)sulfonyl)oxy)biphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trifluoromethanesulfonic anhydride (20.1 mL) was added at 0° C. to a mixture of ethyl 4′-fluoro-2-hydroxy-6-propoxybiphenyl-4-carboxylate (31.5 g) and pyridine (200 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 (44.6 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-e93a7877ec3e4128961b5947be96ccde
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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