2,6-Lutidine → 1-Propene, 3-bromo-2-[(1,1-dimethylethyl)sulfonyl]-

HRID 1290317Notes

Reaction equation

HRID 1290317 reaction equation
[Br:1][CH2:2][CH:3]([S:6]([C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:8])=[O:7])[CH2:4]Br.N1C(C)=CC=CC=1C>C(Cl)Cl>[C:9]([S:6]([C:3](=[CH2:4])[CH2:2][Br:1])(=[O:7])=[O:8])([CH3:12])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 13416236HCID 13416236, compound

Product 1

HCID 112649701-Propene, 3-bromo-2-[(1,1-dimethylethyl)sulfonyl]-Yield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 16.78 g (0.052 mol) of 1,3-dibromo-2-(t-butylsulfonyl) propane and 14 mL (0.12 mol) of 2,6-lutidine in 55 mL of CH2Cl2 was refluxed for 75 minutes. The solution was allowed to cool to room temperature and extracted with three 80-mL portions of 5% HCl followed by 80 mL of water. The organic layer was dried over MgSO41 filtered, and the solvent removed in vacuo from a water bath at 45° C. to give 11.46 g (91%) of the allyl bromide as a white solid, mp 40.5°-42.0° C., which was used without further purification.

Workup

  1. temperaturewas refluxed for 75 minutes
  2. extractionextracted with three 80-mL portions of 5% HCl
  3. customThe organic layer was dried over MgSO41
  4. filtrationfiltered
  5. customthe solvent removed in vacuo from a water bath at 45° C.

Sources & evidence

ORD record
ord-a0f19735eb0a4cd38782c63793987977
Source dataset
uspto-grants-1998_05
Patent number
US05750767

Reaction notes

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