Reaction #45332

Reaction equation

H2O

3-nitro-5-(trifluoromethyl)benzoic acid

borane THF

→

[3-nitro-5-(trifluoromethyl)phenyl]methanol

Solvents

THF

THF

Conditions

Workup

1. 1
   ExtractionThe resultant mixture was extracted with EtOAc (100 mL)
2. 2
   Washthe organic layer was washed with brine (50 mL)
3. 3
   Dryingdried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherPurification by flash chromatography with 50% EtOAc/hexanes

Procedure

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (2.0 g, 8.5 mmol) in THF (100 mL) was added borane-THF (17 mL of a 1 M solution in THF, 17 mmol). The reaction was stirred at 60° C. for 24 hours and then poured into H2O (50 mL). The resultant mixture was extracted with EtOAc (100 mL) and the organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 50% EtOAc/hexanes afforded [3-nitro-5-(trifluoromethyl)phenyl]methanol. Rf=0.35 (75% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) 8.44 (s, 1H), 8.40 (s, 1H), 7.98 (s, 1H), 4.91 (s, 2H), 2.07 (bs, 1H).

Source