4-Bromobiphenyl → N-(3,5-Dimethylphenyl)-N-(4-phenylphenyl)benzophenone hydrazone

HRID 992002Notes

Reaction equation

HRID 992002 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][N:10]=[C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Br[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:27][CH:26]=1.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[C:4]([N:9]([C:34]2[CH:35]=[CH:36][C:31]([C:28]3[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=3)=[CH:32][CH:33]=2)[N:10]=[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)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

6

Reactant 3

HCID 71014-BromobiphenylHCID 207408531-(3,5-Dimethylphenyl)-2-(diphenylmethylene)hydrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 12081749N-(3,5-Dimethylphenyl)-N-(4-phenylphenyl)benzophenone hydrazoneYield 66%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Procedure

N-(3,5-Dimethylphenyl)benzophenone hydrazone (1.0 equiv., 0.5 mmol, 150 mg), 4-bromobiphenyl (1.0 equiv., 0.5 mmol, 117 mg), Pd(OAc)2 (0.01 equiv, 0.005 mmol, 2 mg), DPE-phos (0.01 equiv, 0.005 mmol, 3 mg), and toluene (1 mL) were added to an oven dried test tube and stirred at room temperature for 2 minutes. NaOtBu (1.4 equiv., 0.7 mmol, 67 mg) and an additional 1 mL toluene were then added. The test tube was then capped with a septum, briefly purged with argon (˜1 min.) and then heated to 100° C. under argon for 14 hours. The reaction solution was then cooled to room temperature, diluted with Et2O, filtered through Celite, and concentrated under vacuum to give the crude product as a brown oil. Purification by flash column chromatography (2% EtOAc/Hex) gave the title product as a yellow solid (149 mg, 0.33 mmol, 66% yield).

Workup

  1. customdried test tube
  2. customThe test tube was then capped with a septum
  3. custombriefly purged with argon (˜1 min.)
  4. temperatureheated to 100° C. under argon for 14 hours
  5. temperatureThe reaction solution was then cooled to room temperature
  6. additiondiluted with Et2O
  7. filtrationfiltered through Celite
  8. concentrationconcentrated under vacuum
  9. customto give the crude product as a brown oil
  10. customPurification by flash column chromatography (2% EtOAc/Hex)

Sources & evidence

ORD record
ord-eb8e34a0322c4ea5a4104a7de6460216
Source dataset
uspto-grants-2002_10
Patent number
US06465693B2

Reaction notes

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