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Water → 1-[(E)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]-4-ethoxy-2,3-difluorobenzene

HRID 1841834
Notes
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Reaction equation

HRID 1841834 reaction equation
[F:1]/[C:2](/[CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH3:14])[CH2:8][CH2:7]1)=[C:3](/[F:5])\I.[F:15][C:16]1[C:21]([F:22])=[C:20]([O:23][CH2:24][CH3:25])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C.C1(C)C=CC=CC=1>[F:5]/[C:3](/[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH3:25])=[C:21]([F:22])[C:16]=1[F:15])=[C:2](/[F:1])\[CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][CH3:14])[CH2:8][CH2:7]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 15135235B-(4-Ethoxy-2,3-difluorophenyl)boronic acidHCID 866743031-((Z)-1,2-difluoro-2-iodovinyl)-4-propylcyclohexane

Product 1

HCID 673277251-[(E)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]-4-ethoxy-2,3-difluorobenzene

Reagents, catalysts & solvents 1

HCID 21863594
Toluene ethanol
Solvent

Procedure

6.30 g (20.1 mmol) of 1-((Z)-1,2-difluoro-2-iodovinyl)-4-propylcyclohexane and 4.86 g (24.1 mmol) of 2,3-difluoro-4-ethoxybenzeneboronic acid are refluxed for 19 h together with 1.16 g (1.0 mmol) of tetrakistriphenylpalladium(0) and 20 ml (20 mmol) of sodium carbonate solution (2 M) in 90 ml of ethanol/toluene (2:1). Water is added, and the batch is extracted with MTBE. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1). The further purification is carried out by recrystallisation from n-heptane, giving 1-[(E)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]-4-ethoxy-2,3-difluorobenzene as a colourless solid (m.p. 60° C.).

Workup

  1. extractionthe batch is extracted with MTBE
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed with water
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=4:1)
  7. customThe further purification
  8. customis carried out by recrystallisation from n-heptane

Sources & evidence

ORD record
ord-e459ec64e4d5444990b74c50d79fdd09
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08945420B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes