Quinoline → 2-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran

HRID 2290178Notes

Reaction equation

HRID 2290178 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]([CH3:19])([CH3:18])[C:11]([OH:17])([CH3:16])[CH2:12][CH2:13][CH:14]=[CH2:15])=[CH:6][CH:5]=1.N1C2C(=CC=CC=2)C=CC=1>C(Cl)(Cl)Cl>[Br:1][CH2:15][CH:14]1[CH2:13][CH2:12][C:11]([C:10]([CH3:19])([CH3:18])[CH2:9][O:8][C:7]2[CH:20]=[CH:21][C:4]([Cl:3])=[CH:5][CH:6]=2)([CH3:16])[O:17]1

Participants

5

Reactant 3

HCID 7047QuinolineHCID 24408BromineHCID 135634657-(4-Chlorophenoxy)-5-hydroxy-5,6,6-trimethyl-hept-1-ene

Product 1

HCID 135634662-Bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuranYield 90.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

16 g (0.1 mole) of bromine are added dropwise to 28.2 g (0.1 mole) of 7-(4-chlorophenoxy)-5-hydroxy-5,6,6-trimethyl-hept-1-ene in 200 ml of absolute chloroform at room temperature, with stirring, and 13 g (0.1 mole) of quinoline are then added at -10° C., with cooling. The reaction mixture is stirred at room temperature for a further 2 hours and concentrated in vacuo, the residue is taken up in ether, the mixture is filtered, the filtrate is again concentrated in vacuo and the residue is stirred in a waterbath at 95° C. for 1 hour. The resulting mixture is taken up in ether, the mixture is filtered and the filtrate is washed with 15 percent strength hydrochloric acid and then with water, dried over sodium sulphate and freed from the solvent in vacuo. 32.7 g (90% of theory) of 2-bromomethyl-5-[1-(4-chlorophenoxy)-2-methylprop-2-yl]-5-methyl-tetrahydrofuran are obtained as an oil, which can be used in the next stage without further purification. ##STR114##

Workup

  1. temperaturewith cooling
  2. stirringThe reaction mixture is stirred at room temperature for a further 2 hours
  3. concentrationconcentrated in vacuo
  4. filtrationthe mixture is filtered
  5. concentrationthe filtrate is again concentrated in vacuo
  6. stirringthe residue is stirred in a waterbath at 95° C. for 1 hour
  7. filtrationthe mixture is filtered
  8. washthe filtrate is washed with 15 percent strength hydrochloric acid
  9. dry with materialwith water, dried over sodium sulphate

Sources & evidence

ORD record
ord-0b97a58e86494be9a0c57c3f61dc0f41
Source dataset
uspto-grants-1986_10
Patent number
US04615725

Reaction notes

Loading…