Isobutylene → HCID 21707225, compound

HRID 1594946Notes

Reaction equation

HRID 1594946 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[CH3:13][C:14](=[CH2:16])[CH3:15]>ClCCl.OS(C(F)(F)F)(=O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:14]([CH3:16])([CH3:15])[CH3:13])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 8255IsobutyleneHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 21707225HCID 21707225, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-39 °C

Procedure

To a solution of 6-bromo-2-hydroxynaphthalene (1.5 g, 6.72 mmol) and liquefied iso-butylene (6 mL) in dry dichloromethane (6 mL) at −78° C. was added triflic acid (6 drops). The resulting solution was stirred for 4 hours as it warmed from −78 to 0° C. The reaction was quenched by adding excess saturated aqueous sodium bicarbonate and partitioned between ethyl acetate and brine. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated under vacuum. Purification on silica gel with 25% ether/hexanes gave the title compound (1.64 g, 80%) as a colorless oil.

Workup

  1. customThe reaction was quenched
  2. additionby adding excess saturated aqueous sodium bicarbonate
  3. custompartitioned between ethyl acetate and brine
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customPurification on silica gel with 25% ether/hexanes

Sources & evidence

ORD record
ord-5e64d0cfbc984d80a4edd7b1d1968a8d
Source dataset
uspto-grants-2001_09
Patent number
US06284796B1

Reaction notes

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