Propargyl alcohol → 3-(5-Bromopyridin-2-yl)prop-2-yn-1-ol

HRID 2108034

Reaction equation

HRID 2108034 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11]>C(NCC)C.[Cu]I>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][OH:12])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 693532,5-Dibromopyridine

Product 1

HCID 139797303-(5-Bromopyridin-2-yl)prop-2-yn-1-olYield 80.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8021DiethylamineSolvent

Procedure

Copper (I) iodide (10 mg) was added to a solution of 2,5-dibromopyridine (4.74 g), propargyl alcohol (1.34 g) and BTPC (75 mg) in diethylamine (50 ml) and the mixture stirred overnight (18 h), under nitrogen. The solution was evaporated in vacuo and the residue treated with 8% sodium bicarbonate (50 ml) and partitioned with dichloromethane (3×50 ml). The combined extracts were dried and evaporated and the residual semi-solid purified by FCC. Eluting with ether afforded the title compound (3.43 g) as fawn crystals m.p. 121°-122°.

Workup

  1. customThe solution was evaporated in vacuo
  2. additionthe residue treated with 8% sodium bicarbonate (50 ml)
  3. custompartitioned with dichloromethane (3×50 ml)
  4. customThe combined extracts were dried
  5. customevaporated
  6. customthe residual semi-solid purified by FCC
  7. washEluting with ether

Sources & evidence

ORD record
ord-3b0770f191704598b3c43a06f4196909
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Linked notes

Loading…