Dimethylformamide → HCID 67325346, compound

HRID 1616941

Reaction equation

HRID 1616941 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.Br[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>>[I:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([O:9][CH:11]([CH3:13])[CH3:12])[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 6167555-Iodobenzene-1,3-diol

Product 1

HCID 67325346HCID 67325346, compoundYield 37.8%

Conditions

Temperature
65 °C

Procedure

A mixture of 5-Iodo-benzene-1,3-diol (2 g, 8 mmol), 2-bromopropane (0.88 mL, 9.3 mmol) and potassium carbonate (1.3 g, 9.3 mmol) in DMF (15 mL, 190 mmol) was stirred at 65° C. After 18 h, the mixture was cooled to RT and the solvent was evaporated. The residue was dissolved in DCM, washed with water and brine. The solvent was evaporated and the residue was purified on silica gel using an ISCO instrument and eluting with hexanes:EtOAc (4:1) to afford the title product (841 mg). MS m/z: 279 [M+H]+.

Workup

  1. temperaturethe mixture was cooled to RT
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water and brine
  5. customThe solvent was evaporated
  6. customthe residue was purified on silica gel using an ISCO instrument
  7. washeluting with hexanes:EtOAc (4:1)

Sources & evidence

ORD record
ord-26b89431d05b4ac4a031f081e8aa30ca
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Linked notes

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