Diethyl Ether → 2-Ethoxy-3-fluorobenzaldehyde

HRID 594274Notes

Reaction equation

HRID 594274 reaction equation
[F:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C>[CH2:12]([O:10][C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5877883-Fluorosalicylaldehyde

Product 1

HCID 866956162-Ethoxy-3-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 3-fluoro-2-hydroxybenzaldehyde (5.000 g; 35.70 mmol), iodoethane (11.131 g; 71.40 mmol), and K2CO3 (5.918 g; 42.80 mmol) in anh. DMF (100 ml) was heated to 80° C., under nitrogen, for 3 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 2-ethoxy-3-fluorobenzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.74 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-2fccbf003a4a4f06ba946e967502afa4
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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