Water → 3-(Bromomethyl)pyrene

HRID 1070365ノート

反応式

HRID 1070365 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 12740433-(Bromomethyl)pyrene収率 236.4%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9eee0dfdb83c4661b9b903eb632a880c
出典データセット
uspto-grants-2005_06
特許番号
US06902720B2

反応ノート

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