Réaction #955937

Équation de réaction

EtMgBr

methyl 4-chloro-2-methoxybenzoate

→

methyl 4-ethyl-2-methoxybenzoate

Rendement 50.0%

Solvants

THF

NMP

ether

Conditions de réaction

Traitement

1. 1
   Autregiving a red color
2. 2
   Autrequenched upon the addition of aq. HCl (1M, 50 mL)
3. 3
   ExtractionThe crude product was extracted with ether
4. 4
   Lavagethe combined organic layers were successively washed with water and brine
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Autreevaporated
8. 8
   AutreThe residue was purified on silica gel (Eluent: 30% EtOAc in hexanes)

Mode opératoire

To a solution of methyl 4-chloro-2-methoxybenzoate (example 18d) (4.16 g, 20.8 mmol) in THF (120 mL) and NMP (12 mL) was added under inert atmosphere Iron (III) acetylacetonate (398 mg, 1.17 mmol) giving a red color. Then EtMgBr (29 ml of 1M solution in ether) was added dropwise under vigorous stirring. The mixture turned dark brown and then violet and then was stirred for 15 more min. The reaction was diluted with ether and quenched upon the addition of aq. HCl (1M, 50 mL). The crude product was extracted with ether and the combined organic layers were successively washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified on silica gel (Eluent: 30% EtOAc in hexanes) to give methyl 4-ethyl-2-methoxybenzoate (2.01 g, 50%) as an oil. 1H NMR (300 MHz, dMSO): δ 1.20-1.22(t, 3H), 2.65-2.7 (dd, 2H), 3.9 (s, 3H), 6.8 (s, 1H), 6.97 (m, 1H), 7.7 (m, 1H).

Source