2-Methyl-2-butene → 3-Cyano-4-fluorobenzoic acid

HRID 2192487Notes

Reaction equation

HRID 2192487 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=O.[K+].[F:11][C:12]1[CH:19]=[CH:18][C:17]([CH:20]=[O:21])=[CH:16][C:13]=1[C:14]#[N:15].CC(=CC)C.S(OS([O-])=O)([O-])=[O:28].[Na+].[Na+]>O.C(O)(C)(C)C.C(Cl)Cl>[C:14]([C:13]1[CH:16]=[C:17]([CH:18]=[CH:19][C:12]=1[F:11])[C:20]([OH:28])=[O:21])#[N:15]

Participants

9

Reactant 5

HCID 105532-Methyl-2-buteneHCID 24346Disodium disulfiteHCID 516951Monobasic potassium phosphateHCID 27695822-Fluoro-5-formylbenzonitrileHCID 23668197Sodium Chlorite

Product 1

HCID 27739323-Cyano-4-fluorobenzoic acidYield 98.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Sodium chlorite (1.819 g, 20.12 mmol) and potassium dihydrogen phosphate (0.228 g, 1.676 mmol) in water (20.00 ml) was added to 2-fluoro-5-formylbenzonitrile (Aldrich; 1 g, 6.71 mmol) in t-butanol (20 ml), followed by 2-methyl-2-butene (10.06 ml, 20.12 mmol). The resulting mixture was stirred at room temperature for 2 hrs. A solution of 4.5 g of sodium disulfite in water (100 ml) was then added carefully. DCM (150 ml) was added and phases were separated. The aqueous layer was then extracted once more with DCM (150 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 (1.09 g).

Workup

  1. customphases were separated
  2. extractionThe aqueous layer was then extracted once more with DCM (150 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-b5b52487b3714bb186194a9c65173449
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…