Toluene → HCID 58028435, compound

HRID 449738Notes

Reaction equation

HRID 449738 reaction equation
B(O)(O)[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.Br[C:12]1[S:13][C:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:19]([F:28])[CH:18]=2)=[CH:15][CH:16]=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:28][C:19]1[CH:18]=[C:17]([C:14]2[S:13][C:12]([C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=3)=[CH:16][CH:15]=2)[CH:22]=[CH:21][C:20]=1[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 1140TolueneHCID 79799Tolylboronic acidHCID 516892Sodium BicarbonateHCID 58028434HCID 58028434, compound

Product 1

HCID 58028435HCID 58028435, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 3.54 g (26.0 mmol) of p-tolylboronic acid, 8.50 g (26.0 mmol) of 2-bromo-5-(3-fluoro-4-pentylphenyl)thiophene, 1.50 g (1.30 mmol) of tetrakis(triphenylphosphine)palladium(0) and 33 ml of 2 M sodium hydrogencarbonate soln. in 80 ml of ethanol/toluene=3:2 is heated at 80° C. for 20 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, toluene). The further purification is carried out by recrystallisation from ethanol and n-heptane. 2-(3-Fluoro-4-pentylphenyl)-5-p-tolylthiophene is obtained as a solid having an m.p. of 115° C.

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, toluene)
  7. customThe further purification
  8. customis carried out by recrystallisation from ethanol and n-heptane

Sources & evidence

ORD record
ord-1e4c746ea26247a9bd5a90d72df3bf39
Source dataset
uspto-grants-2013_07
Patent number
US08486297B2

Reaction notes

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