Carbon tetrabromide → HCID 68678819, compound

HRID 2233258Notes

Reaction equation

HRID 2233258 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][N:7]=[CH:6]1.C(Br)(Br)(Br)[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:11][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][N:7]=[CH:6]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68678332HCID 68678332, compound

Product 1

HCID 68678819HCID 68678819, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-hydroxypropyl)-4,5-dihydroimidazole (1.0 g, 3.65 mmol) in tetrahydrofuran (15 ml) was reacted with carbon tetrabromide (1.43 g, 5.47 mmol) and triphenylphosphine (1.43 g, 5.47 mmol) at ambient temperature for 18 hours. Solvent evaporation in vacuo and purification by flash chromatography on silica gel, eluting with 10% methanol in dichloromethane, yielded 1-(3-bromopropyl)-4,5-dihydroimidazole (429 mg, 35% yield) as a white solid:

Workup

  1. customSolvent evaporation
  2. customin vacuo and purification by flash chromatography on silica gel
  3. washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-f30d06a99eed472581c30b9430d65d37
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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