Bromobenzene → 1,1,2-Triphenylhydrazine

HRID 1978273

반응식

HRID 1978273 반응식
Cl.[C:2]1([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CC([O-])(C)C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:17]1([NH:9][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 3

HCID 7961BromobenzeneHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 23676156Sodium t-butoxide

생성물 1

HCID 2390581,1,2-Triphenylhydrazine수율 95%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-촉매HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

1,1-Diphenylhydrazine hydrochloride (1.2 equiv., 0.6 mmol, 135 mg), bromobenzene (1.0 equiv., 0.5 mmol, 0.05 mL), Pd(OAc)2 (0.01 equiv, 0.005 mmol, 2 mg), BINAP (0.01 equiv., 0.005 mmol, 3 mg), and NaOtBu (2.8 equiv., 1.4 mmol, 134 mg) and toluene (3 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.) and then heated to 80° C. for 4 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (5% EtOAc/Hex) to give the title product as a white solid (123 mg, 0.47 mmol, 95% yield).

후처리

  1. customdried test tube which
  2. customwas capped with a septum
  3. custompurged briefly with argon (˜1 min.)
  4. temperatureThe reaction was then cooled to room temperature
  5. additiondiluted with Et2O (2 mL)
  6. filtrationfiltered through Celite
  7. concentrationconcentrated under vacuum
  8. customThe crude mixture was purified by flash column chromatography (5% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-c9eddc8887bb4d75830a9ed8bca4a880
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235936B1

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