1-Bromo-3-chloropropane → HCID 18511640, compound

HRID 1370538Notes

Reaction equation

HRID 1370538 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:3][C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][O:10][CH2:14][CH2:15][CH2:16][Cl:17])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 820684-Fluorophenethyl Alcohol

Product 1

HCID 18511640HCID 18511640, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 86 g (2.14 mol) of NaOH pellets in 86 g of water is stirred, cooled to 25° C. and then treated with 20 g (0.143 mol) of 4-fluorophenethyl alcohol, 113 ml (1.14 mol) of 1-bromo-3-chloropropane and then with 4.85 g (14 mmol) of tetrabutylammonium hydrogen sulfate. Vigorous stirring is maintained for 4 h at 25° C., extraction is then carried out with ether and the extract is washed with water and with aqueous saline solution and dried over anhydrous sodium sulfate. After removing the inorganic salt, the filtrate is evaporated to dryness and the residual oil is rectified under vacuum to give 20.3 g (Yd: 65%) of product of formula 22.1:

Workup

  1. temperatureis maintained for 4 h at 25° C.
  2. extractionextraction
  3. washthe extract is washed with water and with aqueous saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing the inorganic salt
  6. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-c97e21f9f7154a2e80499ae2fc40d77d
Source dataset
uspto-grants-2003_06
Patent number
US06583159B1

Reaction notes

Loading…