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

HRID 1586234Notes

Reaction equation

HRID 1586234 reaction equation
[C:1]([Br:5])(Br)(Br)Br.N1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42]CO)=[CH:36][CH:35]=1)([O-:33])=[O:32]>C(Cl)Cl>[N+:31]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH2:1][Br:5])=[CH:36][CH:35]=1)([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 1049PyridineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5908694-Nitrobenzenebutanol

Product 1

HCID 146450881-(4-Bromobutyl)-4-nitrobenzeneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A.Carbon tetrabromide (34.01 gm, 102.55 mmol), pyridine (8.3 mL, 102.55 mmol) and triphenylphosphine (25.52 gm, 112.55 mmole) were added sequentially to a solution of 4-(4-nitrophenyl) butanol (20.0 gm, 102.55 mmol) in 400 mL of CH2Cl2 (precooled to 0° C.) and was allowed to stir overnight with warming to room temperature. The volatiles were removed under vacuum and the residue dissolved in ethyl acetate, filtered through a plug of silica and concentrated to dryness. The resulting oil was purified by flash chromatography eluting hexane:ethyl acetate(v:v, 4:1) to give 4-(4-nitrophenyl)butyl bromide as an oil 23.51 gm (88%). 1H NMR (CDCl3) 1.95-1.81 (m, 4H), 2.78 (t, 2H), 3.45 (t, 2H), 7.37 (d, 2H), 8.15 (d, 2H).

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue dissolved in ethyl acetate
  3. filtrationfiltered through a plug of silica
  4. concentrationconcentrated to dryness
  5. customThe resulting oil was purified by flash chromatography
  6. washeluting hexane

Sources & evidence

ORD record
ord-1b7dc3b2f12f47ff8d8f577ae7335132
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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