Trifluoromethanesulfonic acid → HCID 68107696, compound

HRID 2364680Notes

Reaction equation

HRID 2364680 reaction equation
[OH:1][C:2]1[C:3]([CH2:15][C:16]([CH3:18])=[CH2:17])=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].FC(F)(F)S(O)(=O)=O>ClCCCl>[CH3:17][C:16]1([CH3:18])[CH2:15][C:3]2=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:2]2[O:1]1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 68107212HCID 68107212, compound

Product 1

HCID 68107696HCID 68107696, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 3-hydroxy-2-(2-methylallyl)-4-nitro-benzoate 4b (2.58 g, 10.30 mmol) was dissolved in 50 mL 1,2-dichloroethane followed by the addition of trifluoromethanesulfonic acid (77 mg, 0.50 mmol). The reaction solution was stirred for 2 hours and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 2,2-dimethyl-7-nitro-3H-benzofuran-4-carboxylate 4c (0.83 g, yield: 32.1%) as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c27a7b21a2ca490892eb33550ecb8228
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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