Hapten, artificial antigen and antibody of pentabrominated diphenyl ethers-121
A pentabromodiphenyl ether and artificial antigen technology, applied in the field of immunochemical analysis, can solve the problem that pentabromodiphenyl ether immunoassay has not been reported, and achieves the effect of high recovery rate and wide application
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Embodiment 1
[0052] Embodiment 1: the synthesis of intermediate compound 4-(tert-butyldimethylsilyloxy) phenylboronic acid
[0053] (1) Under nitrogen protection conditions, add DMF (35mL) to 4-bromophenol (3.46g, 20mmol), tert-butyldimethylsilyl chloride (4.16g, 27.6mmol), imidazole (4.08g, 60mmol) and stirred at room temperature for 8-16 h; after distilling off the solvent under reduced pressure, the residue was poured into a large amount of water and extracted with ethyl acetate (AcOEt); the organic phase was washed with saturated brine, anhydrous Na 2 SO 4 Drying; the solvent was evaporated under reduced pressure, and the residue was separated and purified by silica gel column chromatography [V (petroleum ether): V (AcOEt) = 50: 1] to obtain 3.92 g of colorless oily compound 2 with a yield of 68% .
[0054] 2: 1 H NMR (400MHz, CDCl 3 )δ0.18(s,6H),0.97(s,9H),6.71(d,J=8.80Hz,2H),7.32(d,J=8.40Hz,2H).
[0055] (2) Slowly add n-BuLi (14.4mmol, 2.5mol / L) dropwise to a THF (12mL) solutio...
Embodiment 2
[0057] Example 2: Synthesis of 2,6,2',4',6'-pentabromo-4-hydroxydiphenyl ether
[0058] (1) Stir anhydrous copper acetate (364mg, 2mmol) and dichloromethane (20mL) at room temperature for 0.5h, then add powder type 4 Molecular sieves, compound 3 (1.01g, 4mmol), 2,4,6-tribromophenol (662mg, 2mmol), Et 3 N (1.4mL, 10mmol) and pyridine (0.8mL, 10mmol), and continued to stir the reaction at room temperature for about 4h; TLC tracking showed that the reaction was stopped after the raw materials were completely reacted; the molecular sieves were removed by suction filtration, the solvent was evaporated under reduced pressure, and the residue was passed through Separation and purification by silica gel column chromatography (petroleum ether) to obtain 419 mg of colorless oily 2',4',6'-tribromo-4-(tert-butyldimethylsilyloxy)diphenyl ether with a yield of 39% .
[0059] 4: 1 H NMR (400MHz, CDCl 3 )δ0.17(s,6H),0.97(s,9H),6.67(d,J=8.80Hz,2H),6.75(d,J=8.80Hz,2H),7.74(s,2H).
[0060]...
Embodiment 3
[0064] Embodiment 3: The synthetic method of pentabromodiphenyl ether hapten compound Ia is as follows:
[0065] (1) will K 2 CO 3 (214mg, 1.55mmol) was added to a solution of compound 6 (180mg, 0.31mmol) in acetone (8mL), and the temperature was raised to reflux for 1h; 8 to 16 hours; after filtering the insoluble matter, distill off the acetone under reduced pressure, dissolve the residue with AcOEt, wash the organic phase with saturated brine, anhydrous Na 2 SO 4 Drying; the solvent was evaporated under reduced pressure, and the residue was separated and purified by silica gel column chromatography [V (petroleum ether): V (AcOEt) = 40: 1] to obtain 239 mg of colorless oily compound 7 with a yield of 82%.
[0066] 7: m.p.99-100°C; 1 H NMR (400MHz, CDCl 3 )δ1.28(t, J=7.20Hz, 3H), 2.15~2.19(m, 2H), 2.66(t, J=7.60Hz, 2H), 4.01(t, J=6.00Hz, 2H), 4.16( q,J=7.20Hz,2H),6.95(s,2H),7.77(s,2H).
[0067] (2) Compound 7 (125mg, 0.18mmol), LiOH·H 2 O (23mg, 0.54mmol) was dissolve...
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