Benzyl Bromide → HCID 178517596, compound

HRID 625950Notes

Reaction equation

HRID 625950 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([OH:8])=[N:6][CH:7]=1.[OH-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:9][C:4]1[C:5]([OH:8])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 178515448HCID 178515448, compound

Product 1

HCID 178517596HCID 178517596, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 10.68 g (56.2 mmol) 5-bromopyridine-2,3-diol in 290 mL MeOH was added 1(N) aqueous NaOH solution (56.2 mL). A solution of benzyl bromide (5.07 mL, 42.6 mmol) in MeOH (20 mL) was added dropwise to this mixture. After stirring at room temperature for 6 h, the reaction mixture was partitioned between water and EtOAc. Layers were separated and the aqueous phase was extracted with EtOAc (3×). Combined organic solutions were washed with brine (1×), dried over Na2SO4 and concentrated in vacuo. The resulting solid was recrystallized from MeOH-EtOAc to give 3-(benzyloxy)-5-bromopyridin-2-ol as a white solid (7.9 g, 50%).

Workup

  1. customthe reaction mixture was partitioned between water and EtOAc
  2. customLayers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×)
  4. washCombined organic solutions were washed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting solid was recrystallized from MeOH-EtOAc

Sources & evidence

ORD record
ord-7adccfbf99b24cc49de61d71bece7277
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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