Chloroform → 9-Allylcarbazole

HRID 2061784

반응식

HRID 2061784 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.[OH-].[K+].[CH2:16](Br)[CH:17]=[CH2:18].C(Cl)(Cl)Cl>CS(C)=O>[CH2:18]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH:17]=[CH2:16]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 6854CarbazoleHCID 7841Allyl bromideHCID 14797Potassium Hydroxide

생성물 1

HCID 30903939-Allylcarbazole수율 100%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Carbazole (10.1 g, 0.057 mol) and potassium hydroxide (88% wt pellets, crushed, 7.1 g, 0.11 mol) were stirred in 100 mL DMSO at 50° C. for 30 min before dropwise addition of allyl bromide (14.7 g, 0.118 mol). After 15 min the reaction mixture was poured into a 500 mL separatory funnel containing 100 mL chloroform and washed 5 times with 200 mL water to give, after solvent evaporation at 60° C. under reduced pressure, compound 15 in >99% purity as a dark brown, viscous syrup which solidified upon cooling (11.9 g, 0.057 mol, 100% yield). 1H NMR (300 MHz, CDCl3): δ=8.14-8.06 (m, 2 carbazole H), 7.49-7.32 (m, 4 carbazole H), 7.28-7.19 (m, 2 carbazole H), 6.04-5.90 (m, CH═CH2), 5.19-5.10 (m, Z-HCH═CH), 5.07-4.97 (m, E-HCH═CH), 4.92-4.85 (m, NCH2). 13C NMR (300 MHz, CDCl3): δ=140.34, 132.27, 125.67, 122.90, 120.33, 119.00, 116.74, 108.74, 45.21.

후처리

  1. additionAfter 15 min the reaction mixture was poured into a 500 mL separatory funnel
  2. washwashed 5 times with 200 mL water
  3. customto give
  4. customafter solvent evaporation at 60° C. under reduced pressure, compound 15 in >99% purity as a dark brown, viscous syrup which
  5. temperatureupon cooling (11.9 g, 0.057 mol, 100% yield)

출처 및 근거

ORD 기록
ord-6bb917780b754dc9afb9efe31616f4bc
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283438B2

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