Pyridine → 1-(4-Bromobutyl)-4-nitrobenzene

HRID 1586231Notes

Reaction equation

HRID 1586231 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16](O)[CH2:17][CH2:18][CH3:19])=[CH:12][CH:11]=1)([O-:9])=[O:8].[Br:21]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:21][CH2:19][CH2:18][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 70579Triphenylphosphine dibromideHCID 21217964HCID 21217964, compound

Product 1

HCID 146450881-(4-Bromobutyl)-4-nitrobenzeneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part A. Pyridine (0.66 mL, 8.21 mmol) was added slowly to an ice cooled solution of 4-nitrophenyl butanol (1.0 gm,5.13 mmol) and dibromotriphenylphosphorane (2.8 gm, 6.66 mmol) in 20 mL acetonitrile under a nitrogen atmosphere. The reaction solution was stirred for 1/2 hr and allowed to warm to ambient temperature and stir overnight. The reaction was concentrated invacuo to give a residue. The residue was filtered through a short plug of silica gel and then the product was purifed by flash chromatography on silica gel eluting methylene chloride:hexane (v:v, 50:50), to give 1-bromo-4-(4-nitrophenyl)butane as an oil 1.3 gm (98%) MS 275(M+NH4)+ 1 H NMR (CDCl3): 8.2(d, 2H), 7.4(d, 2H), 3.4(t, 2H), 2.8(t, 2H), 1.8-2.0(m, 4H).

Workup

  1. stirringstir overnight
  2. concentrationThe reaction was concentrated invacuo
  3. customto give a residue
  4. filtrationThe residue was filtered through a short plug of silica gel
  5. washeluting methylene chloride

Sources & evidence

ORD record
ord-58d06552f3b34e6887aefcd4108e4e15
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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