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

HRID 1787457Notes

Reaction equation

HRID 1787457 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].[N+:16]([C:19]1[CH:24]=[C:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH:22]=[CH:21][C:20]=1O)([O-:18])=[O:17].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:25]([C:23]1[CH:22]=[CH:21][C:20]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 18661Phenol, 4-(1,1-dimethylethyl)-2-nitro-HCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium Bicarbonate

Product 1

HCID 231090154-tert-Butyl-2-nitrophenyl trifluoromethanesulfonateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triflic anhydride (4.14 mL, 24.6 mmol) was added dropwise to a solution of 2-nitro-4-tert-butyl phenol (4.00 g, 20.5 mmol) and pyridine (2.16 mL, 26.7 mmol) in CH2Cl2 (50 mL) at 0° C. The yellow solution was stirred 0.25 h at 0° C., poured onto saturated NaHCO3 and extracted with CH2Cl2. The combined extracts were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated. 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.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts were washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe residue was purified by filtration through a plug of silica-gel (methylene chloride)

Sources & evidence

ORD record
ord-b1b942087bf745d3b5ca51230e7c780b
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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