Carbazole → HCID 66780455, 화합물

HRID 572955노트

반응식

HRID 572955 반응식
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:14](Br)([CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:15]>[N+](C)([O-])=O.C1(C)C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[CH3:19][C:18]([CH3:21])([CH2:17][CH:14]([CH3:16])[CH3:15])[CH2:20][C:3]1[CH:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][C:8]([CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:10]=3

참가 물질

6

반응물 2

HCID 6854CarbazoleHCID 11435470Pentane, 2-bromo-2,4,4-trimethyl-

생성물 1

HCID 66780455HCID 66780455, 화합물

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 1140Toluene용매HCID 6375Nitromethane용매

실험 절차

ZnCl2 (36.8 g, 276 mmol) and carbazole (21.0 g, 126 mmol) are suspended in 600 mL nitromethane in a 1 qt jar in a glove-box. The t-octyl bromide (53.4 g, 276 mmol) is added dropwise to the gray-green suspension via addition funnel. The mixture turns into a black solution during the addition. The solution is allowed to stir at room temperature for two hours and then poured into 500 mL ice water. The product is extracted out of the mixture with 500 mL and 250 mL CH2Cl2. The combined organic portions are dried with MgSO4, filtered and rotovapped to yield a dark residue. This residue is taken up in 200 mL toluene, passed through a plug of silica, and washed through with 150 mL toluene. The yellow solution is reduced to a solid on the rotovap. This material is recrystallized from 100 mL hexane at −13° C. 27 g (55%) of white crystals are collected. The crystallization only moderately improved the purity of the product. 1H NMR (CDCl3): δ 8.02 (d, JH-H=1.6 Hz, 2H), 7.80 (br s, 1H, NH), 7.42 (dd, JH-H=8.6, 1.8 Hz, 2H), 7.29 (d, JH-H=8.5 Hz, 2H), 1.83 (s, 4H, CH2), 1.49 (s, 12H, CMe2), 0.72 (s, 18H, CMe3).

후처리

  1. additionThe mixture turns into a black solution during the addition
  2. extractionThe product is extracted out of the mixture with 500 mL and 250 mL CH2Cl2
  3. dry with materialThe combined organic portions are dried with MgSO4
  4. filtrationfiltered
  5. customto yield a dark residue
  6. washwashed through with 150 mL toluene
  7. customThis material is recrystallized from 100 mL hexane at −13° C
  8. custom27 g (55%) of white crystals are collected
  9. customThe crystallization

출처 및 근거

ORD 기록
ord-d6d47f43c6664eb0b1819f204c75ad96
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029487B2

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