Iodoethane → 3-Bromo-5-ethoxypyridine

HRID 1428520Notes

Reaction equation

HRID 1428520 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) and iodoethane (69.0 g, 443 mmol) in DMF (700 mL) was stirred for 16 h at 25° C. Then the mixture was concentrated to give the residue which was extracted with DCM (2×200 mL), dried over Na2SO4 and concentrated to give 3-bromo-5-ethoxypyridine (53 g, 218 mmol, 54.2% 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. customto give the residue which
  3. extractionwas extracted with DCM (2×200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7ef6dbc90d454c19a94b8dcdcce75039
Source dataset
uspto-grants-2015_01
Patent number
US08937071B2

Reaction notes

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