Pyridine → 4-(1,3-Diphenyl-1-propoxy)benzyl bromide

HRID 363017Notes

Reaction equation

HRID 363017 reaction equation
[C:1]1([CH:7]([O:16][C:17]2[CH:24]=[CH:23][C:20]([CH2:21]O)=[CH:19][CH:18]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Br-:31].[Br-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[C:1]1([CH:7]([O:16][C:17]2[CH:24]=[CH:23][C:20]([CH2:21][Br:31])=[CH:19][CH:18]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 12890784Triphenylphosphane dibromideHCID 541185434-(1,3-Diphenyl-1-propoxy)benzyl alcohol

Product 1

HCID 538499334-(1,3-Diphenyl-1-propoxy)benzyl bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice cold solution of 6-5 (1.19 g, 6.0 mmol) in acetonitrile (15 ml) was added pyridine (0.76 g, 9.6 mmol) and then triphenylphosphine dibromide (3.29 g, 7.8 mmol). The mixture was stirred at ice bath temperature for 1/4 hr under N2 and at ambient temperature for 1 &3/4 hrs and then was filtered. Concentration of the filtrate in vacuo gave a crude oil. The pure product 6-6 was obtained after three silica gel chromatographic separations.

Workup

  1. filtrationat ambient temperature for 1 &3/4 hrs and then was filtered
  2. customConcentration of the filtrate in vacuo gave a crude oil

Sources & evidence

ORD record
ord-e3011c2937014a46978d9d92fb3b23c3
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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