1,3-Dibromopropane → HCID 69663449, compound

HRID 2212087Notes

Reaction equation

HRID 2212087 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13](=[O:25])[CH:14]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH3:15].[Br:26][CH2:27][CH2:28][CH2:29]Br>O1CCCC1>[CH3:11][O:12][C:13](=[O:25])[C:14]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:18])([CH3:15])[CH2:29][CH2:28][CH2:27][Br:26]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 2733832Lithium HexamethyldisilazideHCID 109442032-benzenesulfonylpropionic acid methyl ester

Product 1

HCID 69663449HCID 69663449, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 6.6 ml, 6.6 mmol) was added dropwise to a stirred solution of 2-benzenesulfonylpropionic acid methyl ester (1.38 g, 5.7 mmol) in tetrahydrofuran at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (3.17 ml, 31.2 mmol) was added. The mixture was slowly warmed to room temperature and stirred for 4 days. After quenching with satd. aqueous NH4Cl, the mixture was extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica gel (i-hexane-ethyl acetate 5–20%) to give the title product (330 mg, 15%).

Workup

  1. stirringstirred for 4 days
  2. customAfter quenching with satd
  3. extractionaqueous NH4Cl, the mixture was extracted into dichloromethane
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (i-hexane-ethyl acetate 5–20%)

Sources & evidence

ORD record
ord-a46ee2428e86478f8918f6d3a32d7ef2
Source dataset
uspto-grants-2006_09
Patent number
US07101892B2

Reaction notes

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