(+-)-Acenaphthenol → 1-Bromo-acenaphthene

HRID 729772Notes

Reaction equation

HRID 729772 reaction equation
[CH:1]1(O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.P(Br)(Br)[Br:15]>C(OCC)C>[Br:15][CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1

Participants

4

Reactant 2

HCID 22750(+-)-AcenaphthenolHCID 24614Phosphorus tribromide

Product 1

HCID 136344461-Bromo-acenaphthene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Acenaphthen-1-ol (88 mol) was dissolved in diethyl ether (150 mL) and cooled down to 0° C. Phosphorous tribromide (3.2 mL, 35 mmol) was then added slowly under nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at room temperature and cooled to 0° C. The reaction mixture was partitioned with water and diethyl ether. The organic layer was dried over Na2SO4, filtered and the solvent evaporated in vacuo to yield the title compound as a yellow solid.

Workup

  1. temperaturecooled to 0° C
  2. customThe reaction mixture was partitioned with water and diethyl ether
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-251f7f60f020428ab2da2a9d4a7de192
Source dataset
uspto-grants-2009_09
Patent number
US07582649B2

Reaction notes

Loading…