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Sodium Carbonate → 4-(3-Chloro-5-vinylpyridin-2-yl)benzaldehyde

HRID 1430095
Notes
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Reaction equation

HRID 1430095 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].Cl[C:19]1[C:24]([Cl:25])=[CH:23][C:22]([CH:26]=[CH2:27])=[CH:21][N:20]=1>COCCOC.O.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>[Cl:25][C:24]1[C:19]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)=[N:20][CH:21]=[C:22]([CH:26]=[CH2:27])[CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 574168492,3-Dichloro-5-ethenylpyridine

Product 1

HCID 578256984-(3-Chloro-5-vinylpyridin-2-yl)benzaldehydeYield 94.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 80711,2-DimethoxyethaneSolvent

Procedure

4.1 g of Na2CO3 (39 mmol), 2.0 g of 4-formylphenylboronic acid (13 mmol), and 0.45 g of Pd(PPh3)4 were added to 2.5 g of compound (8) (14.9 mmol) prepared in Example 5 dissolved in 50 mL of 1,2-dimethoxyethane and 50 mL of distilled water, and refluxed under heating and stirring for 18 hours. The mixture was cooled to room temperature, and concentrated about 50% under reduced pressure. The aqueous layer was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4) to obtain 3.0 g 4-(3-chloro-5-vinylpyridin-2-yl)benzaldehyde (yield 82%).

Workup

  1. temperatureunder heating
  2. concentrationconcentrated about 50% under reduced pressure
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (eluting solvent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-e9e04adaffb047cfb998a9f4402c8c8d
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940769B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes