4-Hydroxybenzaldehyde → 4-(2-Fluoroethoxy)benzaldehyde

HRID 594266Notes

Reaction equation

HRID 594266 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][CH2:11][CH2:12]I.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-

Product 1

HCID 150586494-(2-Fluoroethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of commercially available 4-hydroxybenzaldehyde (2.000 g; 16.40 mmol), 1-fluoro-2-iodoethane (2.849 g; 16.40 mmol), and K2CO3 (4.527 g; 32.80 mmol) in anh. DMF (30 ml) was heated to 70° C., under nitrogen, for 2.5 h. After cooling to rt, the reaction mixture was filtered over a pad of celite. Et2O was added and the organic layer was washed with water, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording 4-(2-fluoroethoxy)benzaldehyde as a yellow oil. LC-MS (conditions A): tR=0.58 min.; no ionisation.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe reaction mixture was filtered over a pad of celite
  3. additionEt2O was added
  4. washthe organic layer was washed with water
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9eea868a239d40a6befda0c06afd9d43
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…