Triphenylphosphine → HCID 11140657, compound

HRID 1720077Notes

Reaction equation

HRID 1720077 reaction equation
[Br-].C1([PH+](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:21][CH2:22][CH2:23][CH:24]=[CH:25][CH2:26][CH:27]=[CH:28][CH2:29][CH:30]=[CH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[Br:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26]/[CH:27]=[CH:28]\[CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 517696Phosphine, triphenyl-, hydrobromideHCID 54325279HCID 54325279, compound

Product 1

HCID 11140657HCID 11140657, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

(3Z,6Z,9Z)-3,6,9,-Pentadecatrieyl!triphenyl-phosphonium Bromide. Bromo-3,6,9-pentadecatriene (7.0 g, 24.6 mmol) was treated with 7.5 g (28.6 mmol) of triphenylphosphine in 25 mL of acetonitrile. The mixture was heated to 70° C. under nitrogen atmosphere. Following reaction completion (monitor salt formation by TLC; 72 hours) the mixture was dried for 36 hours under reduced pressure to ensure removal of traces of acetonitrile. The resultant yellow residue, 13.45 g, was used in the next reaction without further purification: IR (neat, cm-1) 3010, 2958, 1652, 1191, 723; 1H NMR (CDCl3) δ 7.93-7.61 (m, 15 H), 5.69-5.12 (m, 6H), 4.02-3.91 (m, 2H), 2.69-2.48 (m, 4H), 2.09-1.92 (m, 2H), 1.89-1.72 (m, 2H), 1.46-1.25 (m, 6H), 0.88 (t, J=6.9 Hz, 3H).

Workup

  1. customreaction completion (monitor salt formation by TLC; 72 hours) the mixture
  2. customwas dried for 36 hours under reduced pressure
  3. customremoval of traces of acetonitrile
  4. customThe resultant yellow residue, 13.45 g, was used in the next reaction without further purification

Sources & evidence

ORD record
ord-f4fdda5015e74a26a45db8c5002fb21e
Source dataset
uspto-grants-1996_04
Patent number
US05504107

Reaction notes

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