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

HRID 1721462Notes

Reaction equation

HRID 1721462 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 91,390.602%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 16.78 g (0.052 mmol) 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 MgSO4, 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; IR (KBr) 2980 cm-1, 1480, 1395, 1230, 1100, 970, 730, 640; 1H NMR (CDCl3)δ 1.40 (s, 9H, t-butyl), 4.30 (s, 2H CH2Br), 6.50 (s, 2H, vinyl).

Workup

  1. temperaturewas refluxed for 75 minutes
  2. extractionextracted with three 80-mL portions of 5% HCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo from a water bath at 45° C.

Sources & evidence

ORD record
ord-ef10f1d0d5614d2b8996138908374985
Source dataset
uspto-grants-1996_04
Patent number
US05510491

Reaction notes

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