2-Methyl-2-butene → 3-Cyano-4-(2,2,2-trifluoroethoxy)benzoic acid

HRID 2192486Notes

Reaction equation

HRID 2192486 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].P([O-])(O)(O)=[O:18].[K+].Cl([O-])=O.[Na+].CC(=CC)C.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O.C(Cl)Cl>[C:8]([C:7]1[CH:10]=[C:3]([CH:4]=[CH:5][C:6]=1[O:11][CH2:12][C:13]([F:15])([F:14])[F:16])[C:1]([OH:18])=[O:2])#[N:9]

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 24346Disodium disulfiteHCID 516951Monobasic potassium phosphateHCID 23668197Sodium ChloriteHCID 581499145-Formyl-2-[(2,2,2-trifluoroethyl)oxy]benzonitrile

Product 1

HCID 581498983-Cyano-4-(2,2,2-trifluoroethoxy)benzoic acidYield 417.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

5-formyl-2-[(2,2,2-trifluoroethyl)oxy]benzonitrile (D29; 155 mg, 0.676 mmol) was dissolved in t-butanol (2 ml). A solution of potassium dihydrogen phosphate (23.01 mg, 0.169 mmol) and sodium chlorite (184 mg, 2.029 mmol) in water (2 ml) was added, followed by 2-methyl-2-butene (1.015 ml, 2.029 mmol). The resulting mixture was stirred at room temperature for 4 hrs. A solution of sodium disulfite (450 mg) in water (10 ml) was added carefully. DCM (15 ml) was then added and the phases were separated. The aqueous layer was then extracted once more with DCM (15 ml). The combined organic extracts were passed through a phase separation cartridge, concentrated under vacuum and dried in a vacuum oven to give the title compound as a white solid (173 mg).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous layer was then extracted once more with DCM (15 ml)
  3. customThe combined organic extracts were passed through a phase separation cartridge
  4. concentrationconcentrated under vacuum
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e9d274512a324e3bb9b678ec52eceb8e
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…