Diethyl Ether → 2-Ethoxy-4,6-difluorobenzaldehyde

HRID 594276Notes

Reaction equation

HRID 594276 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([OH:11])[C:3]=1[CH:4]=[O:5].I[CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C.O>[CH2:13]([O:11][C:6]1[CH:7]=[C:8]([F:10])[CH:9]=[C:2]([F:1])[C:3]=1[CH:4]=[O:5])[CH3:14]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 225079192,4-Difluoro-6-hydroxybenzaldehyde

Product 1

HCID 866956172-Ethoxy-4,6-difluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-difluoro-6-hydroxybenzaldehyde (4.340 g; 27.50 mmol), iodoethane (8.562 g; 54.90 mmol), and K2CO3 (4.553 g; 32.90 mmol) in anh. DMF (75 ml) was heated to 80° C., under nitrogen, for 45 min. Et2O and water were added, and the organic layer was further washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 2-ethoxy-4,6-difluorobenzaldehyde as an orange solid. LC-MS (conditions A): tR=0.70 min.; [M+H]+: 187.39 g/mol.

Workup

  1. washthe organic layer was further washed with brine
  2. dry with materialdried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-21e24afd06da4e7ea3e5aa6c63e773b2
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…