Triphenylphosphine → HCID 53875198, compound

HRID 363076Notes

Reaction equation

HRID 363076 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][OH:12].[F:20][C:21]([F:31])([F:30])[O:22][C:23]1[CH:24]=[C:25](O)[CH:26]=[CH:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:21]([F:20])([F:30])[F:31])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27332613-(Trifluoromethoxy)phenolHCID 5363146Diisopropyl azodicarboxylateHCID 113139803-[2,6-Dichloro-4-(3,3-dichloroallyloxy)-phenoxy]-propan-1-ol

Product 1

HCID 53875198HCID 53875198, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.10 g of 3,5-dichloro-4-(3-hydroxypropoxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.56 g of 3-trifluoromethoxyphenol and 0.83 g of triphenylphosphine dissolved in 20 ml of tetrahydrofuran was added dropwise a solution of 0.64 g of diisopropylazodicarboxylate dissolved in 10 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 1.03 g of 3,5-dichloro-4-(3-(4-trifluoromethoxyphenoxy) propoxy)-1-(3,3-dichloro-2-propenyloxy)benzene (64% yield), nD23.4 1.5343.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated
  3. customto obtain a residue

Sources & evidence

ORD record
ord-b12fcb2731b940c182e176972dad1b9d
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

Loading…