Background and overview[1]
(4-Nitrobenzyl)triphenylphosphorus bromide is an organophosphorus compound that can be used as a pharmaceutical synthesis intermediate and can also be used in the preparation of photosensitizers from stearic acid 1801. If (4-nitrobenzyl)triphenylphosphonium bromide is inhaled, move the patient to fresh air; if skin contact occurs, remove contaminated clothing and rinse skin thoroughly with soap and water. If discomfort occurs , seek medical attention; if eye contact occurs, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
Structure
Preparation method[1]
Step 1: Synthesis of p-nitrobenzyl bromide
Add p-nitrotoluene (13.7g, 0.1mol) and 50mL anhydrous CCl4 to a three-neck round-bottomed flask with argon gas. Dissolve After dissolving, add 18.7g Indonesian stearic acid NBS (N-bromosuccinimide, 0.105mmol) and 0.484g BPO (benzoyl peroxide, 0.002mol). The mixture was refluxed for 5 hours and then filtered once the reaction had stopped. The filter cake was washed with hot CCl4. All filtrates were combined and concentrated in vacuo. Recrystallization of the resulting yellow solid gave light yellow needle-shaped crystals. Repeated cycles of concentration and crystallization finally yielded 11.3 g of crystals (52% yield). 1HNMR (CDCl3) δ (ppm): 4.53 (s, 2H), 7.57 (d, 2H), 8.20 (d, 2H). 13CNMR (CDCl3) δ (ppm): 124.04, 129.95, 144.83, 147.68.
Step 2 Synthesis of (4-nitrobenzyl)triphenylphosphorus bromide
Add 5.24gPPh3 (triphenylphosphine, 0.02mol) to a 50mL toluene solution of p-nitrobenzyl bromide (4.32g, 0.02mol). After refluxing for 3 hours, the reaction was cooled to room temperature and the mixture was filtered. The light yellow powder (9.56g, yield 100%) was dried to obtain (4-nitrobenzyl)triphenylphosphonium bromide, which could be used in the next reaction without further purification.
Main reference materials
[1] Chemistry of Materials, 22(11), 3310-3312; 2010
