Benzyl Bromide → 4-(1-Benzyloxy-ethyl)-3,5-dibromo-pyridine

HRID 712706Notes

Reaction equation

HRID 712706 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:11])[C:7]=1[CH:8]([OH:10])[CH3:9].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:10][CH:8]([C:7]1[C:2]([Br:1])=[CH:3][N:4]=[CH:5][C:6]=1[Br:11])[CH3:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 586226311-(3,5-Dibromopyridin-4-yl)ethanol

Product 1

HCID 1176674404-(1-Benzyloxy-ethyl)-3,5-dibromo-pyridineYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 1-(3,5-dibromo-pyridin-4-yl)-ethanol (600 mg, 1.4 mmol) in DMF (12 mL) is added sodium hydride (60% dispersion in mineral oil, 60 mg, 1.5 mmol). After stirring at 0° C. for 30 min, benzyl bromide (281 mg, 1.6 mmol) is added. The reaction is warmed and stirred at room temperature for 16 h. The reaction is quenched with the addition of saturated aqueous NH4Cl and H2O and is extracted with EtOAc. The combined organic layers are dried and concentrated. The crude product is purified by flash column chromatography to provide 306 mg of 4-(1-benzyloxy-ethyl)-3,5-dibromo-pyridine.

Workup

  1. temperatureThe reaction is warmed
  2. stirringstirred at room temperature for 16 h
  3. customThe reaction is quenched with the addition of saturated aqueous NH4Cl and H2O
  4. extractionis extracted with EtOAc
  5. customThe combined organic layers are dried
  6. concentrationconcentrated
  7. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-7cccff68fb824e67a133b4b272f37359
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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