Iodoethane → 3-Bromo-5-ethoxypyridine

HRID 1050110Notes

Reaction equation

HRID 1050110 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:16][CH3:17]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 122934803-Bromo-5-ethoxypyridineYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-bromopyridin-3-ol (70 g, 402 mmol), K2CO3 (111 g, 805 mmol), iodoethane (69.0 g, 443 mmol) in DMF (900 mL) was stirred for 16 h at 25° C. Then the mixture was concentrated and water (100 mL) was added, the mixture was extracted with DCM (400 mL×2), the combined organic phase were dried over Na2SO4, filtered, and concentrated to give 3-bromo-5-ethoxypyridine (53 g, 218 mmol, 54% yield): 1H NMR (400 MHz, CD3OD) δ 8.19-8.17 (m, 2H), 7.60-7.59 (m, 1H), 4.13-4.07 (m, 2H), 1.40 (t, J=7.0 Hz, 3H); ES-LCMS m/z 202 (M+H).

Workup

  1. concentrationThen the mixture was concentrated
  2. additionwater (100 mL) was added
  3. extractionthe mixture was extracted with DCM (400 mL×2)
  4. dry with materialthe combined organic phase were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6565a0115d0d4a2a94b1daf60b57652c
Source dataset
uspto-grants-2016_07
Patent number
US09382238B2

Reaction notes

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