Iodoethane → 3-Chloro-4-ethoxy-5-fluorobenzaldehyde

HRID 387205Notes

Reaction equation

HRID 387205 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[CH:5]=[O:6].[OH-].[K+].I[CH2:15][CH3:16]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[O:10][CH2:15][CH3:16])[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 27827873-Chloro-5-fluoro-4-hydroxybenzaldehyde

Product 1

HCID 201120653-Chloro-4-ethoxy-5-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-Chloro-5-fluoro-4-hydroxybenzaldehyde (1.0 gram, 5.7 mmol) in THF (40 mL) was heated at reflux for 17 hours with KOH (534 mg, 9.5 mmol, 1.7 eq) in water (5 mL) and iodoethane (1 mL, 2.2 eq). The reaction was then transferred to a separatory funnel with water and extracted with methylene chloride (thrice, 150 mL each). The combined organic layers were washed with 10% aqueous HCl (40 mL), dried (MgSO4), and concentrated to a viscous orange liquid to yield 1.13 g of 3-chloro-4-ethoxy-5-fluorobenzaldehyde. 1H-NMR (500 MHz, CDCl3): 9.84 (d, J=1.9 Hz, 1H), 7.71 (t, J=1.6 Hz, 1H), 7.53 (dd, J=1.9, 10.7 Hz, 1H), 4.37-4.32 (m, 2H), 1.47-1.40 (m, 3H).

Workup

  1. extractionextracted with methylene chloride (thrice, 150 mL each)
  2. washThe combined organic layers were washed with 10% aqueous HCl (40 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a viscous orange liquid

Sources & evidence

ORD record
ord-07ea71810f384782b12080664fc650f3
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

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