Benzyl 2-bromoethyl ether synthesis
- Product Name:Benzyl 2-bromoethyl ether
- CAS Number:1462-37-9
- Molecular formula:C9H11BrO
- Molecular Weight:215.09
622-08-2
1462-37-9
Step 2: To a stirred solution of 2-benzyloxyethanol (17.0 g, 111.884 mmol) and triphenylphosphine (35.0 g, 134.21 mmol) in dichloromethane (170 mL) was slowly added N-bromosuccinimide (23.88 g, 134.21 mmol) in batches at a temperature between -10°C and -5°C, keeping the reaction temperature at -10 °C to -5 °C. After the addition was completed, the reaction mixture was continued to be stirred at room temperature for 1 hour until complete consumption of the feedstock was confirmed by thin layer chromatography (TLC) analysis. Upon completion of the reaction, the mixture was concentrated and the crude product was purified by column chromatography (CC) using a petroleum ether solution of 5% ethyl acetate as eluent to afford benzyl 2-bromoethyl ether (13.5 g, 56.2% yield) as a light yellow liquid (TLC conditions: petroleum ether solution of 30% ethyl acetate; Rf value: 0.7).
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Yield:1462-37-9 94.3%
Reaction Conditions:
with lithium bromide in acetonitrile at 70 - 80; for 2.5 h;Reagent/catalyst;Solvent;Temperature;
Steps:
3; 6; 9 Preparation of 2-benzyloxybromoethane
38.6 g of ethyl 2-benzyloxy p-toluenesulfonate (0.126 mol), 32.83 g of lithium bromide (0.378 mol) and 386 mL of acetonitrile were added to a 1000 mL four-necked flask, and the reaction was carried out at 70 ° C - 80 ° C for 2.5 h. The completion of the reaction was monitored by TLC, 300 mL of water was added, the reaction solution was extracted with 200 mL of chloroform three times, the organic phase was combined, washed once with 200 mL of water, and the organic phase was evaporated to give 25.6 g of colorless transparent oil, yield: 94.3%; HPLC purity: 99.9%. The GC purity was 99.9%.
References:
CN109896934,2019,A Location in patent:Paragraph 0041-0043; 0050-0052; 0059-0061
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1462-37-9
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