Ethanol → 3-Bromo-5-ethoxypyridine

HRID 555994Notes

Reaction equation

HRID 555994 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:2]=1.[Br:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([OH:27])[CH:26]=1.C(O)C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:20][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([O:27][CH2:1][CH3:2])[CH:26]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 122934803-Bromo-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (0.461 g, 1.758 mmol) is added to a mixture of 3-bromo-5-hydroxy pyridine (0.3 g, 1.724 mmol) in THF (10 ml). Ethanol (0.103 ml) is added the reaction mixture is cooled to 0° C. (ice-bath). DEAD (0.277 ml, 1.758 mmol) is finally added and the mixture is warmed to room temperature and stirred overnight. The crude material is purified by flash chromatography by wet loading onto a 50 g silica column eluting with 3:1 iso-hexanes:EtOAc to afford the title compound as a yellow oil, [MH+ 201.88].

Workup

  1. temperaturethe mixture is warmed to room temperature
  2. customThe crude material is purified by flash chromatography by wet loading onto a 50 g silica column
  3. washeluting with 3:1 iso-hexanes

Sources & evidence

ORD record
ord-4b566cb152cd4cba8b88a6b8cd957b5d
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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