Methyl iodide → Methyl 3-cyano-4-fluorobenzoate

HRID 1478463Notes

Reaction equation

HRID 1478463 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6]([OH:8])=[O:7])#[N:2].[C:13](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[F:12])[C:6]([O:8][CH3:13])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27739323-Cyano-4-fluorobenzoic acid

Product 1

HCID 45790123Methyl 3-cyano-4-fluorobenzoateYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL rbf was added 3-cyano-4-fluoro-benzoic acid (2.6 g, 15.9 mmol), potassium carbonate (6.6 g, 47.6 mmol), and DMF (30 mL) and the reaction was allowed to stir for 10 minutes. Iodomethane (1.1 mL, 17.5 mmol) was added dropwise and the reaction was allowed to stir for 1 h. The reaction was complete by 1 cms. The reaction was quenched with brine and extracted with EtOAC. The organic layer was washed with brine 3 times and the organic layer was dried over sodium sulfate and evaporated. Methyl 3-cyano-4-fluoro-benzoate (2.5 g, 62%) was isolated as a white solid. ESI-MS m/z calc. 179.0, found 180.0 (M+1)+; Retention time: 1.15 minutes (3 min run).

Workup

  1. stirringto stir for 1 h
  2. customThe reaction was quenched with brine
  3. extractionextracted with EtOAC
  4. washThe organic layer was washed with brine 3 times
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-e8459121bccb4f6380f9b551d36ca067
Source dataset
uspto-grants-2016_08
Patent number
US09403839B2

Reaction notes

Loading…