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Water → 5-Phenylnicotinaldehyde

HRID 594213
Notes
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Reaction equation

HRID 594213 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.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.CCOC(C)=O>[C:10]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=2)[CH:7]=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 155197645-Phenylnicotinaldehyde

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of commercially available 5-bromonicotinaldehyde (5.070 g; 26.43 mmol), phenylboronic acid (4.934 g; 39.65 mmol), and Pd(PPh3)4 (1.527 g; 1.32 mmol) in toluene (65 ml) and aq. 2 M Na2CO3 (59 ml) was heated to reflux, under nitrogen, for 2.5 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (heptane/AcOEt=1/1) afforded 5-phenylnicotinaldehyde as a yellow oil. LC-MS (conditions A): tR=0.61 min.; [M+H]+: 184.48 g/mol.

Workup

  1. temperaturewas heated
  2. temperatureto reflux, under nitrogen, for 2.5 h
  3. extractionThe separated aq. layer was further extracted with AcOEt
  4. washThe mixed organic layers were washed with brine
  5. dry with materialdried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (heptane/AcOEt=1/1)

Sources & evidence

ORD record
ord-0ddef30d073a4906ac32dd937af38151
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242970B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes