Pyridine → HCID 19068276, compound

HRID 1957687Notes

Reaction equation

HRID 1957687 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH2:19]O)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N1C=CC=CC=1.P(Br)(Br)[Br:28]>C1(C)C=CC=CC=1>[C:1]12([C:11]3[CH:12]=[C:13]([CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:19][Br:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 19068253HCID 19068253, compound

Product 1

HCID 19068276HCID 19068276, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.72 g (10 mmol) of the above benzyl alcohol (a), 30 ml of toluene and 800 μl (10 mmol) of pyridine were introduced into a three-necked flask. A solution of 940 μl (10 mmol) of phosphorus tribromide in 9 ml of toluene was added dropwise, at 0° C., and the mixture was stirred at room temperature for 4 hours. The reaction medium was evaporated to dryness and the residue was taken up in water and ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated from hexane, filtered and dried. 2.35 g (70%) of the expected benzyl bromide, having a melting point of 95°-9° C., were recovered.

Workup

  1. customThe reaction medium was evaporated to dryness
  2. customThe organic phase was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated from hexane
  7. filtrationfiltered
  8. customdried
  9. customwere recovered

Sources & evidence

ORD record
ord-198e6c3cff384fc99eddf31e102461b4
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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