Carbon tetrabromide → (RS)-2-(5-(1-Bromoethyl)-isoxazol-3-yl)-pyridine

HRID 707655Notes

Reaction equation

HRID 707655 reaction equation
O[CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=1)[CH3:3].C(Br)(Br)(Br)[Br:16]>ClCCl>[Br:16][CH:2]([C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 11205Carbon tetrabromideHCID 44605541(RS)-2-(5-(1-Hydroxyethyl)-isoxazol-3-yl)-pyridine

Product 1

HCID 67958649(RS)-2-(5-(1-Bromoethyl)-isoxazol-3-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of (RS)-2-(5-(1-hydroxy-ethyl)-isoxazol-3-yl)-pyridine (0.9 gm), and triphenylphosphene (1.77 gm) in dichloromethane (20 ml) was added carbontetrabromide (6 gm) at 0° C. The reaction mixture was stirred at 30° C. over a period of 2.5 h. The reaction was monitored by TLC. The reaction was quenched by addition of water and layers were separated. Combined organic extract was washed with brine and evaporated under vacuum to provide the 1.7 gm crude mass which was purified by using silica gel column chromatography to provide title compound in 0.8 gm quantity (65%).

Workup

  1. customThe reaction was quenched by addition of water and layers
  2. customwere separated
  3. extractionCombined organic extract
  4. washwas washed with brine
  5. customevaporated under vacuum
  6. customto provide the 1.7 gm crude mass which
  7. customwas purified

Sources & evidence

ORD record
ord-2b4b4e6d763a479285439a77f6f2d5df
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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