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Ethanol → 4-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

HRID 895713
Notes
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Reaction equation

HRID 895713 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]#[N:20])[CH:15]=2)[CH:10]=1.[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O)=[O:25].C1(C)C=CC=CC=1.C(O)C>C(=O)([O-])[O-].[Na+].[Na+].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.O>[C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:21]([O-:23])=[O:22])=[CH:3][C:2]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]=[O:25])[CH:18]=[CH:17]2)#[N:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 2921892-Formylphenylboronic acidHCID 223809233-Bromo-4-(6-cyano-2-naphthyloxy)nitrobenzene

Product 1

HCID 223809674-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent
HCID 10340Sodium CarbonateSolvent

Procedure

The compound (3-bromo-4-(6-cyano-2-naphthyloxy)nitrobenzene) (1 g) obtained in a previous production example, 2-formylphenyl boronic acid (610 mg) and tetrakis(triphenylphosphine)palladium (0) (150 mg) were heated to reflux and reacted for 6 hours in a mixture of 2 M sodium carbonate aqueous solution (10 ml), toluene (10 ml) and ethanol (10 ml). After cooling to room temperature, water was added and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1) to obtain 880 mg of 4-(6-cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene.

Workup

  1. temperaturewere heated
  2. temperatureto reflux
  3. extractionextraction
  4. washThe ethyl acetate layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-00b3f9566f0247e989e5a7f00222f09f
Source dataset
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06916837B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes