Hydrochloric Acid → HCID 5312953, compound

HRID 259235Notes

Reaction equation

HRID 259235 reaction equation
O[CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].N1C=CC=CC=1.P(Br)(Br)[Br:18].Cl>CCOCC>[Br:18][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24614Phosphorus tribromideHCID 53128155-Heptynoic acid, 7-hydroxy-

Product 1

HCID 5312953HCID 5312953, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7-hydroxy-5-heptynoic acid (88.2 g), described in Example 78, in anhydrous ether (300 ml) and pyridine (12 ml) is added dropwise phosphorus tribromide (67.5 g) at 10° C. The solution is stirred at room temperature for 30 min. then cooled to 5° C and 10% HCl (120 ml) is added slowly. The organic layer is washed with water and 10% sodium carbonate, dried (Na2SO4) and concentrated. The residue is distilled under reduced pressure to give 7-bromo-5-heptynoic acid, b.p. 146° C, 0.8 mm.

Workup

  1. temperaturethen cooled to 5° C
  2. washThe organic layer is washed with water and 10% sodium carbonate
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-f2c9ce681af94f168c114dfa877b942f
Source dataset
uspto-grants-1977_07
Patent number
US04036856

Reaction notes

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