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Toluene → HCID 22288648, compound

HRID 968307
Notes
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Reaction equation

HRID 968307 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[N:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1C1C=CC=CC=1B(O)O>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>[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[C:9]1[N:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[CH:12]=[CH:11][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 22288640HCID 22288640, compoundHCID 22288643HCID 22288643, compound

Product 1

HCID 22288648HCID 22288648, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent

Procedure

To a toluene (80 mL) solution containing 4-{2-[(6-bromo-2-pyridinyl)oxy]ethoxy}benzaldehyde (1 g) and tetrakis(triphenylphosphine)palladium (0.18 g), a 2M aqueous solution (4 mL) of sodium carbonate and a solution of 2,4-difluorophenylbenzeneboronic acid (0.64 g) in ethanol (4 mL) were added. The resultant mixture was refluxed for four hours. After completion of reaction, the reaction mixture was poured into saturated saline, and the thus-obtained toluene layer of the resultant mixture was separated. The separated layer was dried over magnesium sulfate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column, to thereby yield 0.71 g of the title compound as colorless crystals (yield 64.5%).

Workup

  1. customAfter completion of reaction
  2. additionthe reaction mixture was poured into saturated saline
  3. customthe thus-obtained toluene layer of the resultant mixture was separated
  4. dry with materialThe separated layer was dried over magnesium sulfate
  5. customthe residual solvent was removed through distillation under reduced pressure
  6. customThe thus-yielded residue was purified by means of a silica gel column

Sources & evidence

ORD record
ord-93e75e556a8e4d85a543152013c18b3c
Source dataset
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06958353B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes