Benzyl Bromide → HCID 18799610, compound

HRID 1637786Notes

Reaction equation

HRID 1637786 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CO>[Cl:1][C:2]1[C:7]([O:8][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 107774172-Chloro-3-hydroxy-6-iodopyridine

Product 1

HCID 18799610HCID 18799610, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2-chloro-6-iodo-3-pyridinol (500 mg, 1.96 mmol), and K2CO3 (690 mg, 5.0 mmol) in methanol (5 mL) was added benzyl bromide (510 mg, 3.0 mmol). The reaction was refluxed for 60 minutes and was allowed to cool to 22° C. The mixture was then concentrated in vacuo. The remaining solids were slurried in ethyl acetate and filtered. The filtrate was dried over MgSO4 and concentrated in vacuo to yield 416 mg (61%) of 2-chloro-3-benzyloxy-6-iodo-pyridine.

Workup

  1. temperatureThe reaction was refluxed for 60 minutes
  2. concentrationThe mixture was then concentrated in vacuo
  3. filtrationfiltered
  4. dry with materialThe filtrate was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-889dbba3d8ff4aafbe08352cf6544e67
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

Loading…