Diethyl Ether → 6-Ethoxy-2,3-difluorobenzaldehyde

HRID 594271Notes

Reaction equation

HRID 594271 reaction equation
[F:1][C:2]1[C:9]([F:10])=[CH:8][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>[CH2:13]([O:11][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([F:1])[C:9]([F:10])=[CH:8][CH:7]=1)[CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 212210312,3-Difluoro-6-hydroxybenzaldehyde

Product 1

HCID 107261946-Ethoxy-2,3-difluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 2,3-difluoro-6-hydroxybenzaldehyde (3.000 g; 21.40 mmol), iodoethane (6.679 g; 42.80 mmol), and K2CO3 (3.551 g; 25.70 mmol) in anh. DMF (60 ml) was heated to 80° C., under nitrogen, for 1.5 h. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 6-ethoxy-2,3-difluorobenzaldehyde as a yellow solid. LC-MS (conditions A): tR=0.72 min.; no ionisation.

Workup

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

Sources & evidence

ORD record
ord-0a7b9d0a640c4531874a3c38eb146a0a
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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