Diethyl Ether → 2-Ethoxy-6-fluorobenzaldehyde

HRID 594272Notes

Reaction equation

HRID 594272 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].I[CH2:12][CH3:13].C([O-])([O-])=O.[K+].[K+].CCOCC>CN(C=O)C>[CH2:12]([O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[C:3]=1[CH:4]=[O:5])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27373276-Fluorosalicylaldehyde

Product 1

HCID 38158942-Ethoxy-6-fluorobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of commercially available 2-fluoro-6-hydroxybenzaldehyde (2.500 g; 17.80 mmol), iodoethane (5.566 g; 35.70 mmol), and K2CO3 (2.959 g; 21.40 mmol) in anh. DMF (50 ml) was heated to 80° C., under nitrogen, for 2 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-6-fluorobenzaldehyde as a yellow solid. LC-MS (conditions A): tR=0.66 min.; [M+H]+: 169.14 g/mol.

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-a0d065f09e1043b1a880084c47438555
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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