3-Hydroxybenzaldehyde → HCID 15058630, compound

HRID 594267Notes

Reaction equation

HRID 594267 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[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:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-

Product 1

HCID 15058630HCID 15058630, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of commercially available 3-hydroxybenzaldehyde (2.000 g; 16.40 mmol), 1-fluoro-2-iodoethane (3.849 g; 22.10 mmol), and K2CO3 (4.527 g; 32.80 mmol) in anh. DMF (30 ml) was heated to 70° C., under nitrogen, for 3 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 3-(2-fluoroethoxy)benzaldehyde as a green oil. LC-MS (conditions A): tR=0.62 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-844ce76d774a4efa97ca79964e0ced1b
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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