Ortho-fluoro-azobenzene derivative and preparation method thereof
An azobenzene derivative and ortho-position technology is applied in the field of preparation of ortho-fluorinated azobenzene, which can solve the problems of limiting the application range of azobenzene, easy scattering of ultraviolet rays, biological damage, etc., so as to prolong the recovery half-life, Excellent optical performance, the effect of improving stability
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Embodiment 1
[0031] 1) Preparation of diazonium salt: 1.55g of 4-amino-3-fluorobenzoic acid (10mmol) and 0.4g of NaOH (10mmol) were weighed, dissolved in 30mL of deionized water, and recorded as A. Weigh 0.76g NaNO 2 (11mmol) was dissolved in 10mL deionized water, and 10mL NaNO 2 Slowly added dropwise to A. After being completely dissolved, the solution was added dropwise to 40mL HCl (1mol L -1 ), keep the temperature at 0-5°C, stir and react for 60 minutes to obtain a diazonium salt solution, and store in an ice bath.
[0032] 2) Coupling reaction: weigh 1.11g 3-fluoroaniline (10mmol) (1:1 molar ratio to diazonium salt) and dissolve in HCl (1mol L -1 ), denoted as B; and the above-mentioned diazonium salt solution was slowly added dropwise to B and stirred.
[0033] 3) Adjust pH: prepare NaHCO 3 Saturated aqueous solution; add the aqueous solution dropwise to the above mixed solution to adjust the pH, and adjust the pH to 5-7; continue to stir for 5 hours under ice bath conditions, a...
Embodiment 2
[0036] 1) Preparation of diazonium salt: 3.1 g of 4-amino-3-fluorobenzoic acid (20 mmol) and 0.8 g of NaOH (20 mmol) were weighed, dissolved in 100 mL of deionized water, and recorded as A. Weigh 1.52g NaNO 2 (22mmol) was dissolved in 20mL deionized water, and 20mL NaNO 2 Slowly added dropwise to A. After being completely dissolved, the solution was added dropwise to 80mL HCl (1mol L -1 ), keep the temperature at 0-5°C, stir and react for 60 minutes to obtain a diazonium salt solution, and store in an ice bath.
[0037] 2) Coupling reaction: Weigh 2.22g of 3-fluoroaniline (20mmol) (the molar ratio of diazonium salt is 1:1) and dissolve it in HCl, denoted as B; slowly add the above diazonium salt solution dropwise Stir in B.
[0038] 3) Adjust pH: prepare NaHCO 3 Saturated aqueous solution; add the aqueous solution dropwise to the above mixed solution to adjust the pH, and adjust the pH to 5-7; continue to stir for 8 hours under ice bath conditions, and filter under reduced ...
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