Water → (3-Nitro-5-(trifluoromethyl)phenyl)methanol

HRID 17054

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].B.C1COCC1.O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 60 °C

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).

Workup

extractionThe resultant mixture was extracted with EtOAc (100 mL)
washthe organic layer was washed with brine (50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification by flash chromatography with 50% EtOAc/hexanes

Sources & evidence

ORD record: ord-871adde5e70a454ab25b5529dd7b5246
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737295B2

Linked notes

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