Sodium Bicarbonate → HCID 58028430, compound

HRID 449735Notes

Reaction equation

HRID 449735 reaction equation
[Na+].[CH2:2]([C:6]1[S:10][C:9](OB(O)[O-])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:23]=2)=[CH:18][C:17]=1[F:35].C(=O)([O-])O.[Na+]>C1COCC1.O.CC(OC)(C)C.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>[CH2:2]([C:6]1[S:10][C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:23]=3)=[CH:18][C:17]=2[F:35])=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 66626399HCID 66626399, compoundHCID 131730281HCID 131730281, compound

Product 1

HCID 58028430HCID 58028430, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 15413tert-Butyl methyl etherSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 4.48 g (20.0 mmol) of 5-butylthiophen-2-ylhydroxyboronic acid sodium salt, 7.0 g (19.9 mmol) of 4-bromo-3-fluoro-4′-hexyloxybiphenyl, 3.36 g (40.0 mmol) of sodium hydrogencarbonate and 1.1 g (0.95 mmol) of tetrakis(triphenylphosphine)palladium(0) in 90 ml of THF/water (2:1) is heated under reflux for 19 h. The mixture is diluted with MTBE, and the organic phase is separated off. The aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to completion, and the residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1). The further purification is carried out by recrystallisation from ethanol. 2-Butyl-5-(3-fluoro-4′-hexyloxybiphenyl-4-yl)thiophene is obtained as a colourless wax having an m.p. of 66° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 19 h
  3. customthe organic phase is separated off
  4. extractionThe aqueous phase is extracted with MTBE
  5. washThe combined organic phases are washed with sat. sodium chloride soln
  6. customand dried
  7. concentrationThe solution is concentrated to completion
  8. customthe residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1)
  9. customThe further purification
  10. customis carried out by recrystallisation from ethanol

Sources & evidence

ORD record
ord-818573f66d00447eb16583c88de50a0a
Source dataset
uspto-grants-2013_07
Patent number
US08486297B2

Reaction notes

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