Water → 3-(Bromomethyl)pyrene

HRID 1070365Notes

Reaction equation

HRID 1070365 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 12740433-(Bromomethyl)pyreneYield 236.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9eee0dfdb83c4661b9b903eb632a880c
Source dataset
uspto-grants-2005_06
Patent number
US06902720B2

Reaction notes

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