Hexane → HCID 86583711, compound

HRID 1279898Notes

Reaction equation

HRID 1279898 reaction equation
[Br:1][CH2:2][CH:3]1[CH2:6][CH2:5][CH2:4]1.[C:7]1([P:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCCCCC>C1(C)C=CC=CC=1>[Br-:1].[CH:3]1([CH2:2][P+:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8058HexaneHCID 11776TriphenylphosphineHCID 2734658(Bromomethyl)cyclobutane

Product 1

HCID 86583711HCID 86583711, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (bromomethyl)cyclobutane (4.5 ml, 0.04 mol) in toluene (50 ml) was treated with triphenylphosphine (10.56 g, 0.04 mol) and the mixture stirred at reflux, under a nitrogen atmosphere, for 2 days. The mixture was allowed to cool to room temperature and treated with hexane (50 ml). The solvent was decanted off and further hexane added. The solvent was decanted off again. The solid was washed with diethyl ether (×2) and dried under reduced pressure to afford the title compound as a white solid (6.34 g).

Workup

  1. temperatureat reflux, under a nitrogen atmosphere, for 2 days
  2. customThe solvent was decanted off
  3. additionfurther hexane added
  4. customThe solvent was decanted off again
  5. washThe solid was washed with diethyl ether (×2)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-bf74d47a7abd492aba2bc2ce4dae8459
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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