Ethanol → 5-Bromo-2-ethoxypyridine

HRID 404525Notes

Reaction equation

HRID 404525 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.[CH2:10]([OH:12])[CH3:11]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([O:12][CH2:10][CH3:11])=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 693532,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 8172375-Bromo-2-ethoxypyridineYield 93%

Conditions

Temperature
140 °C

Procedure

Preparation of 5-Br-2-ethoxy pyridine via General Method B (microwave): The general procedure in section 3.1. was followed using sodium metal (0.3 g, 1.3 mmol, 3 eq.) and 2,5-dibromopyridine (0.1 g, 4.22 mmol, 1 eq.) in ethanol (2 mL). The mixture was heated under microwave irradiation at 140° C. for 21 min. Workup as above gave 5-bromo-2-ethoxypyridine (0.80 gm, 93%). Spectral data were identical to those reported above.

Sources & evidence

ORD record
ord-cd827a45b7da49908e26eeeb9ced7247
Source dataset
uspto-grants-2014_06
Patent number
US08748582B2

Reaction notes

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