Pyridine → 4-tert-Butyl-2-nitrophenyl trifluoromethanesulfonate

HRID 735790Notes

Reaction equation

[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[C:16]([C:20]1[CH:25]=[CH:24][C:23](O)=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([C:20]1[CH:25]=[CH:24][C:23]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:22]([N+:27]([O-:29])=[O:28])[CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Triflic anhydride (4.14 mL, 24.6 mmol) was added dropwise to a solution of 4-tert-butyl-2-nitrophenol (4.00 g, 20.5 mmol) and pyridine (2.16 mL, 26.7 mmol) in methylene chloride (50 mL) at 0° C. The yellow solution was stirred 0.25 h at 0° C., poured onto saturated aqueous NaHCO3 and extracted with methylene chloride. The combined extracts were washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtration through a plug of silica-gel (methylene chloride) to provide trifluoro-methanesulfonic acid 4-tert-butyl-2-nitro-phenyl ester (5.82 g, 87%) as a pale yellow oil which was utilized without further purification.

Workup

extractionextracted with methylene chloride
washThe combined extracts were washed with saturated aqueous NaHCO3
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
filtrationThe residue was purified by filtration through a plug of silica-gel (methylene chloride)

Sources & evidence

ORD record: ord-92b71e5b944a48ada13a8cc0ebbbeb58
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592332B2

Reaction notes

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