Allyl bromide → 3-(Allyloxy)-2-chloro-6-(hydroxymethyl)-4-iodopyridine

HRID 1072990Notes

Reaction equation

HRID 1072990 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([I:9])[CH:5]=[C:4]([CH2:10][OH:11])[N:3]=1.[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>CN(C=O)C.CCOC(C)=O>[CH2:16]([O:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH2:10][OH:11])=[CH:5][C:6]=1[I:9])[CH:15]=[CH2:14]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 106845682-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol

Product 1

HCID 220470323-(Allyloxy)-2-chloro-6-(hydroxymethyl)-4-iodopyridineYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol (C2) (7.14 g, 25.0 mmol) is dissolved in DMF (50 mL) in a dry flask under N2, sodium hydride (60% dispersion in mineral oil) (1.0 g, 25.0 mmol) is added, and the reaction is stirred for 1 h at rt. Allyl bromide (2.38 mL, 27.5 mmol) is added, and the reaction mixture is stirred 48 h at rt. The mixture is diluted with EtOAc (50 mL) and washed 4×25 mL of a 50% saturated solution of 1:1 NaCl/NaHCO3. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to a white solid. The solid is washed with hexane and dried to afford 3-(allyloxy)-2-chloro-6-(hydroxymethyl)-4-iodopyridine (C50) as a white solid (68% yield). MS (EI) for C9H9Cl/NO2, m/z: 325 (M)+.

Workup

  1. stirringthe reaction mixture is stirred 48 h at rt
  2. washwashed 4×25 mL of a 50% saturated solution of 1:1 NaCl/NaHCO3
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a white solid
  6. washThe solid is washed with hexane
  7. customdried

Sources & evidence

ORD record
ord-b5fe9c244e054dc187f22728edeedb46
Source dataset
uspto-grants-2005_06
Patent number
US06911543B2

Reaction notes

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