Reaktion #163952

Reaktionsgleichung

NaBH4

3,5-dinitrobenzoic acid

BF3.OEt2

→

title compound 6

Ausbeute 67.1%

(3,5-Dinitrophenyl)methanol

Ausbeute 67.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched with 1 M HCl
2. 2
   ExtraktionThe aqueous phase was extracted with DCM
3. 3
   Waschenthe organic phase was then washed with saturated Na2CO3
4. 4
   TrocknenThe organic phase was dried over MgSO4
5. 5
   Sonstigeevaporated under reduced pressure

Vorschrift

To a suspension of NaBH4 (2.85 g, 75.4 mmol) in dry THF (40 mL) at 0° C. was added a solution of 3,5-dinitrobenzoic acid (8.0 g, 37.7 mmol) in THF (20 mL), followed by the addition of BF3.OEt2 (12.5 mL, 98.0 mmol). The resulting mixture was warmed to 25° C. and stirred for 1 hour after which the reaction was quenched with 1 M HCl. The aqueous phase was extracted with DCM and the organic phase was then washed with saturated Na2CO3. The organic phase was dried over MgSO4 and evaporated under reduced pressure to give the title compound 6 as an orange solid (5.01 g, 25.3 mmol, 67%). 1H NMR (400 MHz, ((CD3)2C)) δ 8.91 (t, J=0.4 Hz, 1H), 8.57 (dd, J=1.2, 2.0 Hz, 2H), 4.93 (d, J=5.2 Hz, 2H), 3.57 (bs, 1H); 13C NMR (75 MHz, (CD3)2CO) δ 149.4, 148.4 (2C), 127.0 (2C), 117.6, 62.8; HRMS (ESI) Calculated for C7H5N2O5 [M−H]−: 197.0204. Found: 197.0200. m.p.: 89° C.

Quelle