Reaktion #166188

Reaktionsgleichung

4-amino-2-chloro-3-methyl-benzoic acid

trimethylsilyldiazomethane

→

title compound

Ausbeute 96.0%

4-Amino-2-chloro-3-methyl-benzoic acid methyl ester

Ausbeute 96.0%

Lösungsmittel

toluene

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   SonstigeThe reaction mixture was quenched by the addition of acetic acid (1 mL)
3. 3
   Waschenthen washed with aqueous saturated sodium bicarbonate solution (10 mL)
4. 4
   Extraktionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
5. 5
   WaschenThe combined organic extracts were washed with brine (20 mL)
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

To a suspension of 4-amino-2-chloro-3-methyl-benzoic acid (0.64 g, 3.45 mmol) in toluene (10 mL) and methanol (10 mL) at 0° C. was added drop-wise trimethylsilyldiazomethane (3.45 mL, 2 M in hexane, 6.90 mmol). The reaction mixture was stirred at 0° C. for 30 min during which the reagents dissolved. The reaction mixture was quenched by the addition of acetic acid (1 mL) then washed with aqueous saturated sodium bicarbonate solution (10 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (0.66 g, 96%). 1H NMR (CDCl3, 400 MHz) 2.26 (3H, s), 3.86 (3H, s), 6.55 (1H, d, J=8.8 Hz), 7.60 (1H, d, J=8.8 Hz).

Quelle