Potassium Iodide → 6-Bromo-2-heptyloxynaphthalene

HRID 650849Notes

Reaction equation

HRID 650849 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.Br[CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH2:20][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 160902-BromoheptaneHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 106157136-Bromo-2-heptyloxynaphthalene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 5 g of 6-bromo-2-naphthol, 50 ml of dimethyl sulfoxide, 3.9 ml of 6-bromoheptane, 7.1 g of potassium iodide and 7.1 g of milled potassium carbonate activated at 80° C. in high vacuum is heated to 65° C. for 16 hours. It is then cooled and is partitioned between ethyl acetate and water and the organic phase is washed several times with water, dried over magnesium sulfate, filtered and evaporated down. Chromatography of the residue over 200 g of silica gel using toluene and subsequent crystallization from toluene/hexane (8:1) give 6-bromo-2-heptyloxynaphthalene.

Workup

  1. customactivated at 80° C. in high vacuum
  2. temperatureIt is then cooled
  3. customis partitioned between ethyl acetate and water
  4. washthe organic phase is washed several times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated down
  8. customtoluene and subsequent crystallization from toluene/hexane (8:1)

Sources & evidence

ORD record
ord-a439ac97b478481185268e40ec081a2a
Source dataset
uspto-grants-2001_08
Patent number
US06277502B1

Reaction notes

Loading…