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Hydrogen Peroxide → 4-Cyano-3,5-difluoro-4'-methoxybiphenyl

HRID 466486
Notes
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Reaction equation

HRID 466486 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:20]=[C:19]([F:21])[C:16]([C:17]#[N:18])=[C:15]([F:22])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].OO>C(O)C.C1C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[C:17]([C:16]1[C:19]([F:21])=[CH:20][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][C:15]=1[F:22])#[N:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 150656534-Cyano-3,5-difluoro-4'-methoxybiphenyl

Reagents, catalysts & solvents 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 241BenzeneSolvent
HCID 702EthanolSolvent

Conditions

Temperature
2 °C

Procedure

A solution of compound 1 (11.50 g, 0.076 mol) in ethanol (90 ml) was added dropwise to a stirred mixture of compound 7 (15.0 g, 0.069 mol) and tetrakis(triphenylphosphine)palladium(O) (2.38 g, 2.06 mmol) in benzene (130 ml) and 2M-sodium carbonate (100 ml) at room temperature under dry nitrogen. The stirred mixture was heated under reflux (90°-95° C.) for 4.5 h (i.e., until glc analysis revealed absence of starting material). The mixture was cooled and stirred for 1 h at room temperature with 30% hydrogen peroxide (2 ml). The mixture was further cooled to 2° C., and the product was filtered off and washed with water. The product was dried (CaCl2) in vacuo to give fawn-coloured needles.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux (90°-95° C.) for 4.5 h (i.e., until glc analysis revealed absence of starting material)
  3. temperatureThe mixture was cooled
  4. filtrationthe product was filtered off
  5. washwashed with water
  6. dry with materialThe product was dried (CaCl2) in vacuo
  7. customto give fawn-coloured needles

Sources & evidence

ORD record
ord-a9b3fef8eaeb466b88be348719a3b928
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05156763

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes