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Chemical Structure| 84337-85-9 Chemical Structure| 84337-85-9

Structure of 84337-85-9

Chemical Structure| 84337-85-9

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Product Details of [ 84337-85-9 ]

CAS No. :84337-85-9
Formula : C15H13BrO2
M.W : 305.16
SMILES Code : O=C(C1=CC=C(C2=CC=C(Br)C=C2)C=C1)OCC
English Name :Ethyl 4'-bromo-[1,1'-biphenyl]-4-carboxylate
MDL No. :MFCD00445192

Safety of [ 84337-85-9 ]

Application In Synthesis of [ 84337-85-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 84337-85-9 ]

[ 84337-85-9 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 64-17-5 ]
  • [ 5731-11-3 ]
  • [ 84337-85-9 ]
YieldReaction ConditionsOperation in experiment
43.79% With sulfuric acid at 130℃; for 10h; Ethyl-4′-bromobiphenyl-4-carboxylate (23) 4-bromobiphenyl-4′-carboxylic acid (64.18 g, 230 mmol, 278 g/mol) was stirred with ethanol (46 g/mol, 500 ml) on an oil bath at temperature 130 °C under reflux. Then few drops of sulphuric acid were added in it and was stirred for 10 h. When whole carboxlic acid dissolved, it was filtered off to get dry product. Dry product was washed with enough cool ethanol to wash out traces of acid. Then the dry product was put in desiccators over night.Yield (30.82 g, 43.79%); M.P. 74.8-75.5 [4].m/z 306 (M+), 278, 261, 153 (100%), 76; δH (400 MHz; CDCl3) 1.42 (3H, t, J 7.1, Me), 4.40 (1H, q,J 7, CHMe), 7.49 (2H, d, J 8.6), 7.59 (2H, d, J 8.61), 7.62 (2H, d, J8.61), 8.11 (2H, d, J8.61), δC (100.5; CDCl3) 14.36, 61.07, 122.52, 126.81, 128.85,130.18, 132.07, 138.94, 144.20, 166.38 (CO);
With sulfuric acid
With sulfuric acid
YieldReaction ConditionsOperation in experiment
at 25℃; sowie bei 40grad.Hydrolysis;
  • 4
  • [ 84337-85-9 ]
  • [ 217086-44-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: NBS / acetone 3: dimethylformamide 4: H2O, OH-
  • 5
  • [ 84337-85-9 ]
  • [ 217086-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 2: NBS / acetone
  • 6
  • [ 84337-85-9 ]
  • [ 217086-47-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 2: NBS / acetone 3: dimethylformamide
YieldReaction ConditionsOperation in experiment
12.8%
  • 8
  • [ 84337-85-9 ]
  • [ 5731-11-3 ]
YieldReaction ConditionsOperation in experiment
83.6% Stage #1: ethyl 4'-bromobiphenyl-4-carboxylate With sodium hydroxide; water In ethanol at 20℃; for 2h; Stage #2: With hydrogenchloride In ethanol; water 2.104b. 2.104b. 4'-bromo-biphenyl-4-carboxylic acid 1.24 mL 2M NaOH solution are added to a solution of 270 mg (0.89 mmol) of ethyl 4'-bromo-biphenyl-4-carboxylate in 10 mL EtOH and the reaction mixture is stirred for 2 h at RT. The pH is adjusted to 6-7 with 1M HCl, the precipitated product is filtered off and dried. Yield: 205 mg (83.6% of theory); C13H9BrO2 (M=277.12); calc.: molar peak (M-H)-: 275/277 fnd.: molar peak (M-H)-: 275/277; Retention time HPLC: 8.5 min (method A).
  • 9
  • [ 5467-74-3 ]
  • [ 94-09-7 ]
  • [ 84337-85-9 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: p-aminoethylbenzoate With tert.-butylnitrite; acetic acid In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 4-Bromophenylboronic acid With tris-(dibenzylideneacetone)dipalladium(0); trifuran-2-yl-phosphane In N,N-dimethyl-formamide at 90℃; for 10h; Inert atmosphere; 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%).
  • 10
  • [ 92-66-0 ]
  • [ 84337-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane 2: hydrogenchloride; bromine; sodium hydroxide 3: sulfuric acid
  • 11
  • [ 5731-01-1 ]
  • [ 84337-85-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; bromine; sodium hydroxide 2: sulfuric acid
 

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