Toluene → HCID 58028440, compound

HRID 449736Notes

Reaction equation

HRID 449736 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[C:12]([F:21])[CH:11]=1.C(=O)([O-])O.[Na+].C1(C)C=CC=CC=1>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:21][C:12]1[CH:11]=[C:10]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[CH:15]=[CH:14][C:13]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27339602-Thiopheneboronic acidHCID 22717522HCID 22717522, compound

Product 1

HCID 58028440HCID 58028440, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 40.0 g (0.31 mol) of thiophen-2-ylboronic acid, 80.0 g (0.32 mol) of 4-bromo-2-fluoro-1-pentylbenzene, 18.0 g (15.6 mmol) of tetrakis(triphenylphosphine)palladium(0) and 400 ml of 2 M sodium hydrogencarbonate soln. in 1000 ml of ethanol/toluene=3:2 is heated at 80° C. for 19 h. Toluene and water are added to the mixture, and the organic phase is separated off. The aqueous phase is extracted with toluene, and the combined organic phases are washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to completion. The residue is purified by column chromatography (SiO2, n-heptane). 2-(3-Fluoro-4-pentylphenyl)thiophene is obtained as a colourless liquid.

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is extracted with toluene
  3. washthe combined organic phases are washed with sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to completion
  6. customThe residue is purified by column chromatography (SiO2, n-heptane)

Sources & evidence

ORD record
ord-04e9e146cd9b47bc8586358942588a10
Source dataset
uspto-grants-2013_07
Patent number
US08486297B2

Reaction notes

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