5-Fluoro-2-nitrobenzoic acid → (5-Fluoro-2-nitrophenyl)methanol

HRID 1264613Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To 5-fluoro-2-nitrobenzoic acid (0.5 g, 2.7 mmol) was added a solution of borane-tetrahydrofuran complex (5 mL, 1.0 M, 5 mmol) and the resulting solution was heated to 70° C. for 3 hours. The reaction was then cooled to room temperature and methanol was added. The mixture was concentrated and methanol was added two additional times to provide 0.48 g (100%) of a white solid. mp 82-86° C. Anal Calc'd for C7H6N3O3F: C, 49.13; H, 3.52; N, 8.18. Found: C, 48.76; H, 3.56; N, 7.88.

Workup

temperatureThe reaction was then cooled to room temperature
concentrationThe mixture was concentrated
additionmethanol was added two additional times

Sources & evidence

ORD record: ord-c7fb689346b3472e8379b0e27605cc50
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544984B1

Reaction notes

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