Water → 1-(bromomethyl)pyrene

HRID 1070365

반응식

HRID 1070365 반응식
[C:1]1([CH2:17]O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.P(Br)(Br)[Br:20].CCOCC.O>C1C=CC=CC=1>[Br:20][CH2:17][C:1]1[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 1049771-Pyrenemethanol

생성물 1

HCID 12740431-(bromomethyl)pyrene수율 236.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A 10.00 g sample (43.1 mmol) of 1-Pyrenemethanol was dissolved in 250 mL of benzene with slight heating. The mixture was returned to room temperature and 1.63 mL (4.24 g, 17.24 mmol) of phosphorus tribromide were slowly added. The mixture was brought to reflux and stirred for 2 h. The mixture was returned to room temperature, and poured into a separatory funnel containing 500 mL 3:2 Et2O:H2O. The organic fraction was washed twice with 100 mL H2O and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to yield 1-(bromomethyl)pyrene (12.030 g, 95.0%) as a dark yellow powder. TLC (SiO2, 1:1 Hexane:EtOAc) Rƒ=0.95. Mp=270° C. (dec) 1H NMR (CDCl3), δ 5.28 (s, 2H), 8.0-8.3 (m, 9H from pyrene). 13C NMR (CDCl3), δ32.643, 123.258-132.374 16 pks from pyrene.

후처리

  1. customwas returned to room temperature
  2. temperatureto reflux
  3. customwas returned to room temperature
  4. additionpoured into a separatory funnel
  5. washThe organic fraction was washed twice with 100 mL H2O
  6. dry with materialdried over anhydrous Na2SO4
  7. customSolvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-9eee0dfdb83c4661b9b903eb632a880c
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06902720B2

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