Bromobenzene → 1,1,2-Triphenylhydrazine

HRID 991994

反応式

HRID 991994 の反応式
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

参加物

7

反応物 3

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

生成物 1

HCID 2390581,1,2-Triphenylhydrazine収率 95%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 634876Binap, (A+-)-触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fa703352cc624706bff5674892a73be7
出典データセット
uspto-grants-2002_10
特許番号
US06465693B2

関連ノート

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