Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 705069

Reaction equation

HRID 705069 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1)(=[O:3])[CH3:2].[CH3:11][Mg]Br.C(OCC)C>O1CCCC1>[Br:10][C:8]1[CH:9]=[C:4]([C:1]([OH:3])([CH3:11])[CH3:2])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (−78° C.) solution of 3-acetyl-5-bromo pyridine (1.98 g, 9.90 mmol) in tetrahydrofuran (33 mL) was added dropwise a solution of methyl magnesium bromide in diethyl ether (3.0 M, 6.60 mL, 19.8 mmol). The reaction was warmed to room temperature, and the resulting mixture was stirred at room temperature overnight. The reaction was then quenched with saturated aqueous ammonium chloride solution and extracted with diethyl ether. The organic extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes) provided the title compound: LCMS m/z 217.83 [M+11]+; 1H NMR (500 MHz, CDCl3) δ 8.61 (s, 1H), 8.53 (s, 1H), 8.01 (d, J=1.9 Hz, 1H), 2.38 (br s, 1H), 1.61 (6H).

Workup

  1. customThe reaction was then quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (0-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-83eeb3bbb294465dae11bfec4f09120d
Source dataset
uspto-grants-2015_11
Patent number
US09173873B2

Linked notes

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