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Sodium Bicarbonate → HCID 58028448, compound

HRID 1943520
Notes
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Reaction equation

HRID 1943520 reaction equation
[Na+].[CH2:2]([C:8]1[S:12][C:11](OB(O)[O-])=[CH:10][CH:9]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:26][CH:25]=2)=[C:20]([F:35])[CH:19]=1.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>[F:35][C:20]1[CH:19]=[C:18]([C:11]2[S:12][C:8]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:9][CH:10]=2)[CH:23]=[CH:22][C:21]=1[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 227175154-Bromo-2-fluoro-4'-pentyl-1,1'-biphenylHCID 131730280HCID 131730280, compound

Product 1

HCID 58028448HCID 58028448, compound

Reagents, catalysts & solvents 3

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

Procedure

A mixture of 3.30 g (13.1 mmol) of 5-hexylthiophen-2-ylhydroxyboronic acid sodium salt, 4.20 g (13.1 mmol) of 4-bromo-2-fluoro-4′-pentylbiphenyl, 2.2 g (26.2 mmol) of sodium hydrogencarbonate and 0.70 g (0.61 mmol) of tetrakis(triphenylphosphine)palladium(0) in THF/water (1:1) is refluxed for 6 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 solution and dried using sodium sulfate. The solution is evaporated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from methanol/-pentane (5:1). 2-(2-Fluoro-4′-pentylbiphenyl-4-yl)-5-hexylthiophene is obtained as a colourless solid having an m.p. of 44° C.

Workup

  1. temperatureis refluxed for 6 h
  2. customthe organic phase is separated off
  3. extractionThe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with sat. sodium chloride solution
  5. customdried
  6. customThe solution is evaporated to dryness
  7. customthe residue is purified by column chromatography (SiO2, n-heptane)
  8. customThe further purification
  9. customis carried out by recrystallisation from methanol/-pentane (5:1)

Sources & evidence

ORD record
ord-a745828eac674d2a92d6f02d31c3e488
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394293B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes