Isopropyl iodide → Methyl 3-fluoro-4-isopropoxybenzoate

HRID 1405384Notes

Reaction equation

HRID 1405384 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH:20]([CH3:22])[CH3:21])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 58551191Methyl 3-fluoro-4-isopropoxybenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To methyl 3-fluoro-4-hydroxy-benzoate (2.00 g, 11.8 mmol) in DMF (12.5 mL) was added K2CO3 (6.50 g, 47.0 mmol) followed by 2-iodopropane (2.35 mL, 23.5 mmol). The mixture was heated at 60° C. for 1.5 h. The mixture was filtered using EtOAc and the filtrate was evaporated under reduced pressure. The residue was dissolved in EtOAc and was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give methyl 3-fluoro-4-isopropoxybenzoate. ESI-MS m/z calc 212.1, found 213.3 (M+1)+. Retention time: 1.70 minutes (3 min run).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwas washed with water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-971222e263c44532a652c82f92a55dcc
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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