1-Bromopentane → 3-Bromo-(1-hexenyl)benzene

HRID 36150Notes

Reaction equation

HRID 36150 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.[Br:31][C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH:35]=O>O1CCCC1.CCCCCC>[Br:31][C:32]1[CH:33]=[C:34]([CH:35]=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 80571-BromopentaneHCID 11776TriphenylphosphineHCID 765833-BromobenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 539400723-Bromo-(1-hexenyl)benzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To 14.7 gm of the Wittig salt prepared from 1-bromopentane and triphenylphosphine in 80 ml of tetrahydrofuran at 0° C. is added 22.5 ml of n-butyl lithium (1.6M) in hexane. The mixture is stirred for 15 minutes, and 3.8 ml of 3-bromobenzaldehyde is added. This mixture is stirred for 30 minutes; and after concentrating and diluting with ether, the solids are filtered off. Further concentration of the filtrate and chromatography over silica gel eluting with 3:2 hexane:ether yields pure 3-bromo-(1-hexenyl)benzene as a clear oil.

Workup

  1. stirringThis mixture is stirred for 30 minutes
  2. concentrationand after concentrating
  3. additiondiluting with ether
  4. filtrationthe solids are filtered off
  5. concentrationFurther concentration of the filtrate and chromatography over silica gel eluting with 3:2 hexane

Sources & evidence

ORD record
ord-907786de66e8486ebf44bf7e5b2f4f54
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Reaction notes

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