2-Fluoro-5-nitrobenzyl alcohol 96

Uses

2-Fluoro-5-nitrobenzyl alcohol may be used to synthesize 2-fluoro-5-nitrobenzyl bromide and 5-amino-2-fluorobenzyl alcohol.

General Description

2-Fluoro-5-nitrobenzyl alcohol can be prepared from 2-fluoro-5-nitrobenzaldehyde.

Synthesis

General steps for the synthesis of 2-fluoro-5-nitrobenzyl alcohol from 2-fluoro-5-nitrobenzaldehyde: Step A: Preparation of (2-fluoro-5-nitrobenzyl)methanol To a solution of 2-fluoro-5-nitrobenzaldehyde (1000 mg, 5.91 mmol) in methanol (10 mL) was added sodium borohydride (182 mg, 4.82 mmol). The reaction mixture was stirred at 0 °C for 3 hours. Upon completion of the reaction, the reaction mixture was acidified to pH 4 with 1 M hydrochloric acid and then concentrated. 50 mL of water was added and the product was extracted with ether. The organic layer was dried with magnesium sulfate, filtered and the solvent was evaporated. The target compound (2-fluoro-5-nitrophenyl)methanol was obtained as a light yellow solid (1007 mg, 99% yield) with a melting point of 62-64 °C. 1H NMR (300 MHz, CDCl3) δ 8.43 (dd, 6-CH, J = 6.2 Hz and 2.9 Hz, 1H), 8.19 (ddd, J = 9 Hz, 4.5 Hz and 2.9 Hz, 1H), 7.20 (dd, J = 9.0 Hz and 9.0 Hz, 1H), 4.85 (d, J = 3.6 Hz, 2H), 2.12 (s, 1H). 13C NMR (75 MHz, CDCl3) δ 125.0 (CH, d, J = 10.0 Hz), 124.7 (CH, d, J = 6.9 Hz), 116.2 (CH, d, J = 23.6 Hz), 58.2 (CH2).

References

[1] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 235 - 239
[2] Patent: WO2011/73322, 2011, A1. Location in patent: Page/Page column 48
[3] Patent: US2017/369489, 2017, A1. Location in patent: Paragraph 0453; 0465
[4] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 2, p. 547 - 550
[5] Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11462 - 11474