Thionyl Chloride → HCID 54474351, compound

HRID 1655632Notes

Reaction equation

HRID 1655632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:14])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][Cl:14])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 54176324HCID 54176324, compound

Product 1

HCID 54474351HCID 54474351, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-bromo-3-pyridinyl)prop-2-en-1-ol (0.85 gms, 3.97 mmol) is diluted with methylene chloride (20 mls). Thionyl chloride (0.27 mls, 97%, leq) is added at room temperature. After one hour a second equivalent of thionyl chloride is added. The reaction is neutralized with saturated aqueous NaHCO3 after an additional hour and extracted with methylene chloride. The organic layer is dried over Na2SO4 and evaporated to yield 0.70 gms of an oil (76%). 1H NMR (CDCl3, 300 MHz) δ 8.90 (s,1H), 8.70 (s,1H), 8.40 (s,1H), 6.70 (m,2H), and 4.30 (d, J=3.8 Hz, 2H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-9a4234c13743457b903c9f5ab07f55c4
Source dataset
uspto-grants-1993_10
Patent number
US05250700

Reaction notes

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