Dimethyl Sulfate → HCID 16091236, compound

HRID 532157Notes

Reaction equation

HRID 532157 reaction equation
[Li+].[CH3:2]C([N-]C(C)C)C.[Cl:9][C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12]([Cl:17])[CH:11]=1.COS(OC)(=O)=O>C1COCC1>[Cl:9][C:10]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12]([Cl:17])[C:11]=1[CH3:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 764241,3-Dichloro-5-iodobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 16091236HCID 16091236, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the mixture of LDA (5 mL, 8.6 mmol) in THF (20 mL) was added compound 1,3-dichloro-5-iodobenzene (2.35 g, 8.6 mmol) under −78° C. Then the mixture was added to the pre-cooled solution of (CH3)2SO4 (12 mL, 10.3 mmol) in THF (10 mL) under −78° C. The solution was concentrated under vacuum. The residue was diluted with EA, washed with 1N HCl, 1N NaOH, brine, dried over Na2SO4, concentrated under vacuum to give the desired product (2.3 g, 93% yield).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additionThe residue was diluted with EA
  3. washwashed with 1N HCl, 1N NaOH, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-27421eacd31f4e7c81cf1f2965547142
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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