Triphenylphosphine → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-bromophenoxy) propyloxy)benzene

HRID 363069Notes

Reaction equation

HRID 363069 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].[Br:16][C:17]1[CH:27]=[CH:26][C:20]([O:21][CH2:22][CH2:23][CH2:24]O)=[CH:19][CH:18]=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:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:24][CH2:23][CH2:22][O:21][C:20]1[CH:19]=[CH:18][C:17]([Br:16])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 187610183-(4-Bromophenoxy)propan-1-ol

Product 1

HCID 537706483,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-bromophenoxy) propyloxy)benzeneYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.30 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.24 g of 3-(4-bromophenoxy)-1-propanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diisopropylazodicarboxylate dissolved in 5 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 0.34 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(4-bromophenoxy) propyloxy)benzene (65% yield), nD25.0 1.5917.

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-c791cd02ff114542bb619cb58c800b4a
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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