Triphenylphosphine → HCID 21466310, compound

HRID 260778Notes

Reaction equation

HRID 260778 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:19].[Br:22][C:23]([Br:27])=[CH:24][CH2:25]O.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>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH3:18])=[CH:14][CH:15]=2)[CH:6]=[CH:5][C:4]=1[O:19][CH2:25][CH:24]=[C:23]([Br:27])[Br:22]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 15853103HCID 15853103, compoundHCID 21466203HCID 21466203, compound

Product 1

HCID 21466310HCID 21466310, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution prepared by dissolving 0.55 g of 2-trifluoromethyl-4-(4-ethoxyphenoxy)phenol, 0.40 g of 3,3-dibromoallyl alcohol and 0.49 g of triphenylphosphine in 10 ml of tetrahydrofuran, a solution prepared by dissolving 0.38 g of diisopropylazodicarboxylate in 5 ml of tetrahydrofuran was added dropwise at room temperature with stirring. After stirring at room temperature for 12 hours, the reaction solution was concentrated. Then, 20 ml of diethyl ether was added thereto, and the precipitate was filtered off. The resulting filtrate was concentrated, and subjected to silica gel column chromatography to give 0.30 g of 2-trifluoromethyl-4-(4-ethoxyphenoxy)-1-(3,3-dibromo-2-propenyloxy)benzene, yield 32%; nD24.0 1.5480.

Workup

  1. customTo a solution prepared
  2. customa solution prepared
  3. additionwas added dropwise at room temperature
  4. stirringAfter stirring at room temperature for 12 hours
  5. concentrationthe reaction solution was concentrated
  6. additionThen, 20 ml of diethyl ether was added
  7. filtrationthe precipitate was filtered off
  8. concentrationThe resulting filtrate was concentrated

Sources & evidence

ORD record
ord-6827ffe57f97477a86c5bb36550099f2
Source dataset
uspto-grants-1996_06
Patent number
US05530015

Reaction notes

Loading…