1-Bromo-4-butylbenzene → 4'-Butyl[1,1'-biphenyl]-4-propanoic acid, ethyl ester

HRID 727505

Reaction equation

HRID 727505 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.C([Li])(C)(C)C.I[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=1>C1COCC1.CCOCC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20][CH:19]=2)=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 3

HCID 5210591-Bromo-4-butylbenzeneHCID 15661143Ethyl 3-(4-iodophenyl)propanoateHCID 178418306HCID 178418306, compound

Product 1

HCID 867491224'-Butyl[1,1'-biphenyl]-4-propanoic acid, ethyl esterYield 91%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3.20 g (15.0 mmol) of 1-bromo-4-butylbenzene (Aldrich Chemical Company #33, 576-2) at -78° C. under argon was added, dropwise over 30 min, 18.0 mL (30.6 mmol, 1.7M in pentane) of t-butyllithium solution. The resulting light yellow solution was warmed to 0° C. and stirred for 1 h. To this solution was added 3.4 g (25 mmol) of thrice-fused zinc chloride in 20 mL of THF. The resulting slurry was stirred for 30 min and then a solution of 2.0 g (6.5 mmol) of 4-iodobenzenepropanoic acid, ethyl ester (Example 43, Part B) and 0.4 g (0.35 mmol) of tetrakis(triphenylphosphine)-palladium(0) in 5 mL of THF was added. The reaction was stirred for 16 h, diluted with ether and washed once with 10% citric acid. The organic phase was dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel (5×20 cm column) eluted with 1:1 hexanes/dichloromethane gave title compound as a colorless oil, 1.79 g , 91% yield.

Workup

  1. stirringThe resulting slurry was stirred for 30 min
  2. stirringThe reaction was stirred for 16 h
  3. washwashed once with 10% citric acid
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (5×20 cm column)
  7. washeluted with 1:1 hexanes/dichloromethane

Sources & evidence

ORD record
ord-4e6663c7803a4b28b15e5f6584edf45e
Source dataset
uspto-grants-1998_01
Patent number
US05712396

Linked notes

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