Dimethyl Sulfate → HCID 16091236, compound

HRID 1750777Notes

Reaction equation

HRID 1750777 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-4d839b9824124615a775641a06bd9f2a
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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