Reaktion #965872

Reaktionsgleichung

methyl 4-iodo-2-methoxybenzoate

DIBALH

NH4Cl

→

title compound

Ausbeute 31.2%

(4-iodo-2-methoxyphenyl)methanol

Ausbeute 31.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with ethyl acetate twice
2. 2
   WaschenThe organic phase was then washed with brine
3. 3
   Trocknendried with anhydrous Na2SO4
4. 4
   SonstigeSolvent was removed
5. 5
   Sonstigethe resulting residue purified by flash column chromatograph

Vorschrift

A solution of methyl 4-iodo-2-methoxybenzoate (840 mg, 2.88 mmol) in THF was purged with nitrogen and cooled to −78° C. DIBALH (6 mL, 5.75 mmol, 1M in toluene) was added slowly. The mixture was then stirred at the same temperature for an hour. Saturated aqueous NH4Cl solution was added, followed by extraction with ethyl acetate twice. The organic phase was then washed with brine and dried with anhydrous Na2SO4. Solvent was removed and the resulting residue purified by flash column chromatograph to give 237 mg of the title compound (31%). 1H NMR (400 MHz, CDCl3): δ 2.17 (1H, s), 3.84 (3H, s), 4.62 (2H, d, J=4.0 Hz), 7.01 (1H, d, J=7.6 Hz), 7.18 (1H, s), 7.29 (1H, d, J=8.0 Hz).

Quelle