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

HRID 992002ノート

反応式

HRID 992002 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-eb8e34a0322c4ea5a4104a7de6460216
出典データセット
uspto-grants-2002_10
特許番号
US06465693B2

反応ノート

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