Toluene → 4-Bromo-3,5-dimethylpyridine

HRID 75236Notes

Reaction equation

HRID 75236 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][N+:5]([O-])=[CH:4][C:3]=1[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 124930364-Bromo-3,5-dimethylpyridin-1-ium-1-olate

Product 1

HCID 223232464-Bromo-3,5-dimethylpyridineYield 38%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To a microwave tube was added 4-bromo-3,5-dimethylpyridine 1-oxide (2.00 g, 9.90 mmol), triphenylphosphine (3.12 g, 11.9 mmol) and toluene (10 mL). The tube was sealed and heated at 180° C. overnight. The reaction solution was diluted with ethyl acetate, and filtered. The filtrate was concentrated and purified by flash chromatography (10% to 40% ethyl acetate in hexanes) to afford the desired product as a yellow oil (700 mg, 38%). 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 2 H), 2.38 (s, 6 H); LCMS calculated for C7H9BrN(M+H)+: m/z=186.0.

Workup

  1. customThe tube was sealed
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography (10% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cf7958424b63469085f6a1986694f0c3
Source dataset
uspto-grants-2014_09
Patent number
US08835423B2

Reaction notes

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