Hexane → 1-(6-Bromo-pyridin-3-yl)-1-pyridin-4-yl-ethanol

HRID 535308Notes

Reaction equation

HRID 535308 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Br:10])=[N:8][CH:9]=1)(=[O:3])[CH3:2].I[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.[Li]CCCC.CCCCCC>C1COCC1>[Br:10][C:7]1[N:8]=[CH:9][C:4]([C:1]([C:17]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)([OH:3])[CH3:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 707143-IodopyridineHCID 156681955-Acetyl-2-bromopyridineHCID 178418339Butyllithium

Product 1

HCID 867184351-(6-Bromo-pyridin-3-yl)-1-pyridin-4-yl-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-acetyl-2-bromopyridine (Aldrich) (1.2 g, 5.82 mmol) and 3-iodopyridine (EGA-Chemie) (1.193 g, 5.82 mmol) in THF (10 ml) was immersed in a dry ice-acetone bath. n-BuLi (1.6M) in hexane (4.00 ml, 6.40 mmol) was added slowly by a syringe at −70° C. (exothermic reaction!). The reaction was allowed to warm up slowly to room temperature and was stirred over night. The reaction mixture was cooled to −20° C. and quenched with H2O before dilution with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo and dried to obtain title compound as off-white solid.

Workup

  1. custom(exothermic reaction!)
  2. temperatureThe reaction mixture was cooled to −20° C.
  3. customquenched with H2O before dilution with ethyl acetate
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customdried

Sources & evidence

ORD record
ord-8a2205192cb94f40af9d52b68d7895c4
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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