Reaktion #43255

Reaktionsgleichung

HCl

Ethyl 3-bromo-2-methylbenzoic acid

ethyl 3-bromo-2-methylbenzoic acid

Methanol

→

(3-bromo-2-methylphenyl)methanol

Ausbeute 90.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAdd 5 equivalents of borane tetrahydrofuran complex
2. 2
   TemperaturThe mixture was refluxed for two hours
3. 3
   Temperaturcooled in an ice bath
4. 4
   SonstigeThe solvent was removed
5. 5
   Sonstigethe mixture partitioned between ethyl acetate and water

Vorschrift

Ethyl 3-bromo-2-methylbenzoic acid was reduced as follows: Add 5 equivalents of borane tetrahydrofuran complex, via syringe, to 10 mmol ethyl 3-bromo-2-methylbenzoic acid in tetrahydrofuran (5 mL). The mixture was refluxed for two hours, then cooled in an ice bath. Methanol (10 mL) was added dropwise, followed by 1 N HCl (50 mL). The solvent was removed and the mixture partitioned between ethyl acetate and water. The yield was 90%. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) 67.5 (d, 1H) 7.2 (d, 1H) 7.1 (t, 1H), 4.6 (s, 2H) 2.3 (s, 3H).

Quelle