Iodopyrazine → (2-Bromo-3-methylphenyl)(pyrazin-2-yl)methanol

HRID 1029010Notes

Reaction equation

HRID 1029010 reaction equation
I[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([Mg]Cl)CCC.[Br:14][C:15]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18]>C1COCC1>[Br:14][C:15]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]([C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1)[OH:18]

Participants

5

Reactant 3

HCID 642841IodopyrazineHCID 137070762-Bromo-3-methylbenzaldehydeHCID 178418265HCID 178418265, compound

Product 1

HCID 67325817(2-Bromo-3-methylphenyl)(pyrazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-iodopyrazine (0.48 mL, 4.85 mmol) in dry THF (3 mL) was brought to 0° C. followed by the slowly addition of butylmagnesium chloride, 2.0M solution in THF (2.4 mL, 4.85 mmol). The resulting dark solution was stirred at 0° C. for 30 min then a solution of 2-bromo-3-methylbenzaldehyde (1.06 g, 5.34 mmol) in THF (2 mL) was slowly added and kept at 0° C. for 2 h. The mixture was quenched with saturated NH4Cl and extracted with DCM. The combined organics were washed with brine, dried over Na2SO4, filtered, concentrated and purified by silica gel column chromatography using gradient 1:1 hexanes/EtOAc to afford a yellow-orange oil as (2-bromo-3-methylphenyl)(pyrazin-2-yl)methanol.

Workup

  1. customwas brought to 0° C.
  2. waitkept at 0° C. for 2 h
  3. customThe mixture was quenched with saturated NH4Cl
  4. extractionextracted with DCM
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a364388c7ef24303ba52162ba3bb3b4b
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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