ethyl 1-(3-bromophenyl)cyclopentanecarboxylate synthesis
- Product Name:ethyl 1-(3-bromophenyl)cyclopentanecarboxylate
- CAS Number:885068-62-2
- Molecular formula:C14H17BrO2
- Molecular Weight:297.19
110-52-1
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Yield:885068-62-2 91%
Reaction Conditions:
Stage #1: ethyl 2-(3-bromophenyl)acetatewith sodium hydride;18-crown-6 ether in N,N-dimethyl-formamide; for 0.416667 h;
Stage #2: 1,4-dibromo-butane in N,N-dimethyl-formamide at 20; for 18 h;
Steps:
74.2
Step 2. Sodium hydride (60% in oil, 1.07 g, 26.8 mmol) is added to a solution of (3-bromo-phenyl)- acetic acid ethyl ester [2.59 g, 10.7 mmol] and 18-crown-6 (catalytic amount) in N5N'- dimethylformamide (50 mL). The mixture is stirred for 25 minutes and 1,4-dibromobutane (1.41 mL, 11.8 mmol) is added dropwise via syringe. The mixture is stirred for 18 hours at ambient temperature, diluted with water (100 mL) and extracted thrice with EtOAc (60 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1 -(3-bromo-phenyl)- cyclopentanecarboxylic acid ethyl ester [2.9 g, 91%] as an oil, which is used without further purification.
References:
WO2006/44732,2006,A2 Location in patent:Page/Page column 197-198
1878-67-7
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