Toluene → HCID 58028435, compound

HRID 1943524Notes

Reaction equation

HRID 1943524 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

Conditions

Temperature
80 °C

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 solution 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 solution. The solution is dried using sodium sulfate and evaporated to dryness. 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 solution
  4. customThe solution is dried
  5. customevaporated to dryness
  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-8b10d813280141c184d951a5081ffd7a
Source dataset
uspto-grants-2013_03
Patent number
US08394293B2

Reaction notes

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