Pyridine → HCID 19756480, compound

HRID 1587771Notes

Reaction equation

HRID 1587771 reaction equation
[C:1]([CH:3]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH2:4]O)#[N:2].N1C=CC=CC=1.P(Br)(Br)[Br:20]>C(Cl)Cl>[C:1]([CH:3]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH2:4][Br:20])#[N:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 19756485HCID 19756485, compound

Product 1

HCID 19756480HCID 19756480, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 24 g (0.11 mol) 2-cyano-2-(4-bromophenyl)-ethanol and 4.5 g (0.055 mol) pyridine in 100 ml CH2Cl2 are slowly added, at -5° to 0°, 12 g (0.044 mol) PBr3. The mixture is stirred for 3 hours at room temperature, thereafter for 2 hours at 40°, allowed to cool off, then poured into 500 ml ice water and extracted with CH2Cl2. The extract is washed with water, dried and evaporated. The resulting residue is chromatographed over a silica gel column with hexane/diethylether 6:4. The glassy residue obtained after evaporation is worked up in toluene and thereafter ether to give the title compound in the form of a yellow powder, m.p. 171° (decomposing).

Workup

  1. additionare slowly added, at -5° to 0°
  2. waitfor 2 hours at 40°
  3. temperatureto cool off
  4. extractionextracted with CH2Cl2
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated
  8. customThe resulting residue is chromatographed over a silica gel column with hexane/diethylether 6:4
  9. customThe glassy residue obtained
  10. customafter evaporation

Sources & evidence

ORD record
ord-8036ced249694ac989fedb2974d52246
Source dataset
uspto-grants-1993_06
Patent number
US05219876

Reaction notes

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