Water → 1-Bromo-2-nonadecyne

HRID 1885459Notes

Reaction equation

HRID 1885459 reaction equation
[CH2:1](O)[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].N1C=CC=CC=1.P(Br)(Br)[Br:28].O>CCOCC>[Br:28][CH2:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24614Phosphorus tribromideHCID 10967930Nonadec-2-yn-1-ol

Product 1

HCID 197643871-Bromo-2-nonadecyne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 18.8 g of 2-nonadecyn-1-ol, 110 ml of ether, 1.14 ml of pyridine and 5.7 ml of phosphorous tribromide in 25 ml of ether is heated at reflux for 2 hours, then stirred at room temperature for 2 hours, poured into water and washed with hydrochloric acid. The solution is evaported and filtered through silicon dioxide with hexane, to give 16.9 g of the desired product as a white solid, mp. 34°-35° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. washwashed with hydrochloric acid
  4. filtrationfiltered through silicon dioxide with hexane

Sources & evidence

ORD record
ord-d43997f77f4a4e969eb81ee6f9dc6ef7
Source dataset
uspto-grants-1992_09
Patent number
US05144045

Reaction notes

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