Carbon tetrabromide → 3-(2-Bromoethoxy)pyridine

HRID 2192354Notes

Reaction equation

HRID 2192354 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9]O)[CH:2]=1.C(Br)(Br)(Br)[Br:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:12][CH2:9][CH2:8][O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 219089972-(Pyridin-3-yloxy)ethan-1-ol

Product 1

HCID 106795983-(2-Bromoethoxy)pyridineYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(pyridin-3-yloxy)-ethanol (200 mg) in 5 mL dichloromethane was cooled to 0° C. and treated with carbon tetrabromide (524 mg) followed by triphenylphosphine (415 mg) portionwise. The reaction mixture was stirred at 0° C. for 30 mins then at room temperature for 45 mins. The volatiles were evaporated and the residue purified by silica gel chromatography eluting with 0-100% EtOAc/pentane to give the title compound (204 mg) as a colourless liquid which was used without further purification.

Workup

  1. waitat room temperature for 45 mins
  2. customThe volatiles were evaporated
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 0-100% EtOAc/pentane

Sources & evidence

ORD record
ord-16c25788f19d41d7b4f90dc81d9742d4
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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