1-Naphthaleneethanol, 8-bromo- synthesis
- Product Name:1-Naphthaleneethanol, 8-bromo-
- CAS Number:80859-61-6
- Molecular formula:C12H11BrO
- Molecular Weight:251.12
75-21-8
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Yield:80859-61-6 56.9%
Reaction Conditions:
Stage #1: 1,8-dibromonaphthalenewith n-butyllithium in tetrahydrofuran;hexane at -70; for 0.5 h;Inert atmosphere;
Stage #2: oxirane in tetrahydrofuran at 0; for 1 h;Inert atmosphere;
Steps:
12.1 Step 1:
Under nitrogen protection, add 1,8-dibromonaphthalene (4 g, 13.99 mmol) and tetrahydrofuran (40 mL) to the round-bottomed flask.Cool it to -70°C,To the above solution was added dropwise a 2.5M solution of butyllithium in n-hexane (6.15 mL, 15.39 mmol). After the addition was complete, the reaction was stirred at -70°C for 30 minutes.To this was added dropwise a 3M solution of ethylene oxide in tetrahydrofuran (28 mL, 84 mmol). After the dropwise addition, the reaction was warmed to 0°C,Stir for 1 hour.To this was added ice water (100 mL).Extract with ethyl acetate (50 mL×3).The organic phase was washed with saturated brine,Dry with anhydrous sodium sulfate and concentrate to obtain crude product,The crude product was purified by flash silica column (ethyl acetate/petroleum ether: 0-40%)2-(8-Bromonaphthalen-1-yl)ethane-1-ol (2 g, yield: 56.9%) was obtained,Yellow solid.
References:
WO2022/194245,2022,A1 Location in patent:Page/Page column 54-55
17135-74-9
270 suppliers
$8.00/250mg
80859-61-6
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