4'-BROMO-BIPHENYL-4-CARBOXYLIC ACID ETHYL ESTER synthesis
- Product Name:4'-BROMO-BIPHENYL-4-CARBOXYLIC ACID ETHYL ESTER
- CAS Number:84337-85-9
- Molecular formula:C15H13BrO2
- Molecular Weight:305.1665
Yield:84337-85-9 50%
Reaction Conditions:
Stage #1: p-aminoethylbenzoatewith tert.-butylnitrite;acetic acid in N,N-dimethyl-formamide at 20; for 0.0833333 h;Inert atmosphere;
Stage #2: 4-Bromophenylboronic acidwith tris-(dibenzylideneacetone)dipalladium(0);trifuran-2-yl-phosphane in N,N-dimethyl-formamide at 90; for 10 h;Inert atmosphere;
Steps:
General procedure.
Pd2dba3 (23 mg, 2.5 mol %), P (2-furyl)3 (46 mg, 20 mol %), and benzeneboronic acid 2c (146 mg, 1.2 equiv) were weighed in a 25 mL Schlenk round bottle flask under nitrogen atmosphere. The system was degassed four times by oil pump. Ethyl 4-aminobenzoate 1n (165 mg, 1 mmol) was weighed in another 25 mL Schlenk round bottle flask under nitrogen atmosphere. DMF (2 mL), tBuONO (108 mg, 1.05 equiv), and HOAc (60 mg, 1.0 equiv) were added in succession by syringe and this reaction mixture was stirred for 5 min. Then the solution containing the newly generated diazonium salt was transferred to the above Schlenk round bottle by syringe. In the course of this transfer, another 2 mL DMF was added to the reaction system. The resulting reaction solution was stirred at 90 °C for 10 h. The solution was then concentrated under reduced pressure and the crude residue was purified by flash column chromatography (petroleum ether/EtOAc = 30:1) to afford the product ethyl biphenyl-4-carboxylate 3o (113 mg, 50%).
References:
Mo, Fanyang;Qiu, Di;Jiang, Yubo;Zhang, Yan;Wang, Jianbo [Tetrahedron Letters,2011,vol. 52,# 4,p. 518 - 522] Location in patent:scheme or table
![4'-Bromo-[1,1'-biphenyl]-4-carboxylic acid](/CAS/GIF/5731-11-3.gif)
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