Diphenylmethylidenehydrazine → Diphenylmethanone (4-fluoro-2-methoxyphenyl)hydrazone

HRID 1677052Notes

Reaction equation

HRID 1677052 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH3:10].[C:11](=[N:24][NH2:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:25][N:24]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:3]([O:9][CH3:10])[CH:4]=1

Participants

8

Reactant 4

HCID 79304DiphenylmethylidenehydrazineHCID 27245202-Chloro-5-fluoroanisoleHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 86626061Diphenylmethanone (4-fluoro-2-methoxyphenyl)hydrazone

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-5-fluoroanisole (0.52 ml, 4.10 mmol), benzophenone hydrazone (0.98 g, 5.00 mmol), sodium-tert-butoxide (561 mg, 5.80 mmol), in toluene (8.0 ml) was charged with Pd2(dba)3 (77.0 mg, 0.08 mmol) and 2-(di-t-butylphosphino)biphenyl (50.0 mg, 0.17 mmol) and heated to 80° C. under argon. The mixture was stirred overnight and checked with LCMS and TLC. The mixture was allowed to cool to room temperature and the reaction mixture was diluted with EtOAc (20 ml) and filtered. Material was used crude in the next step.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-a20268727ef24aefa71916a5e30b6d6d
Source dataset
uspto-grants-2011_08
Patent number
US08008279B2

Reaction notes

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