Dimethylformamide → HCID 67798546, compound

HRID 1527452Notes

Reaction equation

HRID 1527452 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8](O)=[CH:7][C:3]=1C(O)=O.[C:13]([O-:16])([O-])=[O:14].[K+].[K+].[CH3:19]I.CN([CH:24]=[O:25])C>CCOC(C)=O>[CH3:19][O:16][C:13](=[O:14])[C:9]1[CH:8]=[C:7]([O:25][CH3:24])[CH:3]=[C:2]([F:1])[C:10]=1[F:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 265967652,3-Difluoro-5-hydroxybenzoic acid

Product 1

HCID 67798546HCID 67798546, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,3-difluoro-5-hydroxy-benzoic acid [749230-51-1] (1.00 g, 5.74 mmol; Melford Laboratories Ltd) in DMF (20 mL) was added K2CO3 (1.99 g, 14.4 mmol) and MeI (0.79 mL, 12.6 mmol), followed by stirring at RT overnight. The reaction mixture was diluted with EtOAc, the organics were washed with a saturated aqueous NH4Cl solution (50 mL) and a saturated aqueous NaHCO3 solution, dried (Phase separator) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:1) to afford the title compound as a colorless oil. TLC, Rf (c-hexane/EtOAc 3:1)=0.37; MS (LC/MS): 203.0 [M+H]+; tR (HPLC conditions c): 4.72 min.

Workup

  1. washthe organics were washed with a saturated aqueous NH4Cl solution (50 mL)
  2. dry with materiala saturated aqueous NaHCO3 solution, dried (Phase separator)
  3. customevaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel (c-hexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-e73d457beeb74514bcf216855fb2df92
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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