Phosphorus tribromide → HCID 13044953, compound

HRID 745685Notes

Reaction equation

HRID 745685 reaction equation
[CH2:1](O)[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].P(Br)(Br)[Br:17]>CCOCC.N1C=CC=CC=1>[Br:17][CH2:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 13044972(Z)-8-tetradecen-2-yn-1-ol

Product 1

HCID 13044953HCID 13044953, compoundYield 219.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

By the procedure of example 14, 3.82 g (18.34 mmol) of (Z)-8-tetradecen-2-yn-1-ol, 72 mg of dry pyridine, and 1.66 g (6.12 mmol) of phosphorous tribromide were reacted in 20 ml of ether under reflux for 2.0 h. It was worked up as described in example 14 to give 3.83 g of crude product. It was purified by evaporative distillation at 105° C.-120° C./0.25 mm to yield 3.64 g (73% by weight yield) of (Z)-1-bromo-8-tetradecen-2-yne as a colorless oil.

Workup

  1. temperatureunder reflux for 2.0 h
  2. customto give 3.83 g of crude product
  3. distillationIt was purified by evaporative distillation at 105° C.-120° C./0.25 mm

Sources & evidence

ORD record
ord-7141f4d79b0d44659564446017b9a551
Source dataset
uspto-grants-1986_07
Patent number
US04599443

Reaction notes

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