Phosphorus oxychloride → HCID 57545162, compound

HRID 1661519Notes

Reaction equation

HRID 1661519 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:17][C:18]2[CH:23]=[C:22]([O:24][CH2:25][CH3:26])[CH:21]=[C:20]([O:27][CH2:28][CH3:29])[CH:19]=2)[C:14](O)=[O:15])=[CH:9][CH:8]=1>[Cl-].[Zn+2].[Cl-]>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[C:14](=[O:15])[C:19]3[C:20]([O:27][CH2:28][CH3:29])=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[CH:23][C:18]=3[O:17]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 57545186HCID 57545186, compound

Product 1

HCID 57545162HCID 57545162, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
0 °C

Procedure

38 ml (407 mmol) of phosphoryl chloride are added to 16.1 g (40.7 mmol) of (4-bromophenyl)-(3,5-diethoxyphenoxy)acetic acid under argon at RT. The mixture is cooled to 0° C., and 8.32 g (61.0 mmol) of zinc chloride are added. After 10 min, the ice bath is removed and the mixture is stirred at RT overnight. The reaction mixture is poured into a large amount of ice-water and stirred for 15 min. Dichloromethane is added, the phases are separated, and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. Gradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 10.2 g (67% of theory) of the product.

Workup

  1. customthe ice bath is removed
  2. additionThe reaction mixture is poured into a large amount of ice-water
  3. stirringstirred for 15 min
  4. additionDichloromethane is added
  5. customthe phases are separated
  6. washthe organic phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customGradient chromatography on silica gel 60 (mobile phase: toluene/ethyl acetate) results in 10.2 g (67% of theory) of the product

Sources & evidence

ORD record
ord-ba41be3091794db1802e9047f4348809
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

Loading…