2-(Dimethylamino)ethanol → 2-Bromo-4-phenylpyridine

HRID 1158706Notes

Reaction equation

HRID 1158706 reaction equation
CN(C)CCO.C([Li])CCC.[C:12]1([C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Br)(Br)(Br)[Br:25]>CCCCCC.O>[Br:25][C:22]1[CH:23]=[C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=[CH:20][N:21]=1

Participants

7

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11205Carbon tetrabromideHCID 136514-PhenylpyridineHCID 178418339Butyllithium

Product 1

HCID 1047002-Bromo-4-phenylpyridineYield 45.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-dimethylaminoethanol (5.60 g, 62.8 mmol) in hexane (80 ml) was added dropwise 1.6N hexane solution of n-butyl lithium (78.5 ml, 125 mmol) under ice-cooling, and stirred at 0° C. for 30 minutes. Then, 4-phenylpyridine (3.24 g, 20.8 mmol) was added thereto, and stirred at 0° C. for 1 hour. After cooling the reaction solution to −78° C., a solution of carbon tetrabromide (25.0 g, 75.4 mmol) in hexane (40 ml) was added thereto, and stirred at −78° C. for 1 hour, then at room temperature for 1 hour. To the reaction solution was added water under ice-cooling, and extracted with ether. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduce pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give the titled compound 2.21 g (45.4%) as solid product.

Workup

  1. temperaturecooling
  2. stirringstirred at 0° C. for 1 hour
  3. temperatureAfter cooling the reaction solution to −78° C.
  4. stirringstirred at −78° C. for 1 hour
  5. waitat room temperature for 1 hour
  6. temperaturecooling
  7. extractionextracted with ether
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled away
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9d562519b434426ca73f9acfdde51242
Source dataset
uspto-grants-2010_10
Patent number
US07812025B2

Reaction notes

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