HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Carbonate → HCID 58160694, compound

HRID 1943514
Notes
Print preview

Reaction equation

HRID 1943514 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19](B(O)O)=[C:18]([F:25])[CH:17]=2)=[CH:12][CH:11]=1)[CH2:8][CH3:9].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)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>[CH2:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:2]3[S:3][CH:4]=[CH:5][CH:6]=3)=[C:18]([F:25])[CH:17]=2)=[CH:12][CH:11]=1)[CH2:8][CH3:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 138512-BromothiopheneHCID 53402576B-(3-Fluoro-4'-propyl(1,1'-biphenyl)-4-yl)boronic acid

Product 1

HCID 58160694HCID 58160694, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 21863594
Toluene ethanol
Solvent

Procedure

A mixture of 25.3 g (0.16 mol) of 2-bromothiophene, 40.0 g (0.16 mol) of 4′-propyl-3-fluoro-4-biphenylboronic acid, 8.5 g (7.4 mmol) of tetrakis(triphenylphosphine)palladium(0) and 170 ml of 2 N sodium carbonate solution in 420 ml of toluene/ethanol (1:2) is refluxed for 18 h. After cooling, the organic phase is separated off, and the aqueous phase is extracted a number of times with toluene. The combined organic phases are washed with water and sat. sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:toluene=9:1). The further purification is carried out by recrystallisation from ethanol and n-heptane, giving 2-(4′-propyl-3-fluorobiphenyl-4-yl)thiophene as a colourless solid (m.p. 88° C.).

Workup

  1. temperatureis refluxed for 18 h
  2. temperatureAfter cooling
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted a number of times with toluene
  5. washThe combined organic phases are washed with water and sat. sodium chloride solution
  6. customThe solution is dried
  7. customevaporated to dryness
  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 and n-heptane

Sources & evidence

ORD record
ord-b4374e14821b4f45b42b5d0526e9b7ca
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394293B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes