Iodoethane → 3-Ethoxy-5-ethyl-2-fluorobenzaldehyde

HRID 1438158Notes

Reaction equation

HRID 1438158 reaction equation
[Si]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])(C(C)(C)C)(C)C.[F-].[K+].I[CH2:23][CH3:24]>CN(C=O)C.CCOC(C)=O>[CH2:23]([O:8][C:9]1[C:10]([F:19])=[C:11]([CH:14]=[C:15]([CH2:17][CH3:18])[CH:16]=1)[CH:12]=[O:13])[CH3:24]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 522689Potassium FluorideHCID 598380723-{[tert-Butyl(dimethyl)silyl]oxy}-5-ethyl-2-fluorobenzaldehyde

Product 1

HCID 579428023-Ethoxy-5-ethyl-2-fluorobenzaldehydeYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 118C (244 mg, 0.87 mmol) in DMF (2.0 mL) was added potassium fluoride (100 mg) and iodoethane (0.13 mL). The mixture was stirred at rt overnight. It was diluted with EtOAc and the organic extracts were washed with brine and dried. The crude product was purified by column chromatography to give 118D (158 mg, 100% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (t, J=7.69 Hz, 3H) 1.46 (t, J=7.03 Hz, 3H) 2.62 (q, J=7.47 Hz, 2H) 4.13 (q, J=7.03 Hz, 2H) 7.02 (dd, J=7.91, 2.20 Hz, 1H) 7.22 (dd, J=5.27, 2.20 Hz, 1H) 10.35 (s, 1H).

Workup

  1. washthe organic extracts were washed with brine
  2. customdried
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5d5db87ccb1747ba9fae5a82e0bda9b6
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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