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ChemicalBook CAS DataBase List 1-Benzyl-4-iodo-1H-pyrazole
50877-42-4

1-Benzyl-4-iodo-1H-pyrazole synthesis

5synthesis methods
4-Iodopyrazole

3469-69-0

Benzyl bromide

100-39-0

1-Benzyl-4-iodo-1H-pyrazole

50877-42-4

Step 1. Synthesis of 1-benzyl-4-iodo-1H-pyrazole; 4-iodo-1H-pyrazole (17 g, 87.63 mmol, 1.00 eq.) was dissolved in N,N-dimethylformamide (150 mL) in a 250 mL round bottom flask. Sodium hydride (3.6 g, 105.00 mmol, 1.20 eq., 70% dispersed in mineral oil) was added in batches at 0 °C. Subsequently, benzyl bromide (16.5 g, 96.49 mmol, 1.10 eq.) was added dropwise at the same temperature. The reaction mixture was slowly warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched with an ice-water mixture (200 mL). The reaction mixture was extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give 1-benzyl-4-iodo-1H-pyrazole as a yellow solid (22 g, 80% yield).

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Yield: 79%

Reaction Conditions:

with tetrabutylammomium bromide;potassium hydroxide at 20; for 48 h;

Steps:

5.2 Preparation of 1-benzyl-4-iodopyrazole
0.323 g of benzyl chloride was added dropwise to a solution of 57.0 g of 4-iodopyrazole, 20.0 g of potassium hydroxide and 2.9 g of TBAB in a solution at room temperature, After the dropwise addition, the mixture was stirred at about constant temperature for about 48 hours. The organic layer was washed three times with 40 ° C water and dried over magnesium sulfate to give 66.0 g of a yellow oil product with a GC purity of 97.0% and a yield of 79%.

References:

Dalian AllyChem Co.,Ltd(AllyChem);WANG, XIANXUE;ZHENG, PENG CN103601749, 2016, B Location in patent:Paragraph 0062-0063

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