ChemicalBook CAS DataBase List 1-(3-BROMOPHENYL)CYCLOPENTANECARBOXYLIC ACID

1-(3-BROMOPHENYL)CYCLOPENTANECARBOXYLIC ACID synthesis

6synthesis methods

Product Name:1-(3-BROMOPHENYL)CYCLOPENTANECARBOXYLIC ACID
CAS Number:143328-23-8
Molecular formula:C12H13BrO2
Molecular Weight:269.13

885068-62-2 Synthesis

ethyl 1-(3-bromophenyl)cyclopentanecarboxylate

885068-62-2
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1-(3-BROMOPHENYL)CYCLOPENTANECARBOXYLIC ACID

143328-23-8
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Yield:143328-23-8 80.6%

Reaction Conditions:

Stage #1: 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl esterwith lithium hydroxide in tetrahydrofuran;methanol;water; for 18 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;methanol;water; pH=1;Acidic aqueous solution;

Steps:

74.3

Step 3. A mixture of l-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl ester [3.42 g, 11.51 mmol], lithium hydroxide (579 mg, 13.81 mmol), THF (13 mL), MeOH (13 mL) and water (13 mL) is vigorously stirred for 18 hours. The mixture is concentrated and the residue is diluted with water (50 mL). The aqueous mixture is acidified with concentrated HCl to pH 1 and extracted twice with EtOAc (50 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1 -(3 -bromo-phenyP-cyclopentanecarboxy lie acid [2.5 g, 80.6%] as a solid, which is used without further purification.

References:

WO2006/44732,2006,A2 Location in patent:Page/Page column 198

143328-18-1 Synthesis