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

HRID 992002노트

반응식

HRID 992002 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-eb8e34a0322c4ea5a4104a7de6460216
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465693B2

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