Methanesulfonyl chloride → HCID 53403083, compound

HRID 58356Notes

Reaction equation

HRID 58356 reaction equation
S(Cl)(C)(=O)=O.[I:6][C:7]1[C:14]([I:15])=[CH:13][C:12]([I:16])=[CH:11][C:8]=1[CH2:9]O.C(N(C(C)C)CC)(C)C.[Cl-:26].[Li+]>ClCCl.O>[I:6][C:7]1[C:14]([I:15])=[CH:13][C:12]([I:16])=[CH:11][C:8]=1[CH2:9][Cl:26]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 34957432,3,5-Triiodobenzyl alcohol

Product 1

HCID 53403083HCID 53403083, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Mesyl chloride (4.24 ml, 56 mmol) was added dropwise into a suspension of 2,3,5-triiodobenzyl alcohol 1 (9.72 g, 20 mmol) in dry dichloromethane (140 ml) containing diisopropylethylamine (11 ml, 64 mmol) and lithium chloride (4.24 g, 100 mmol) at 0° C. under dry nitrogen gas flow. The reaction mixture was stirred 5 h at room temperature, then cold H2O (100 mL) was added. The resulting aqueous phase was extracted with dichloromethane (2×10 ml). The combined organic extracts were washed with NaHCO3 aq (20 ml) and H2O (20 ml) then dried (Na2SO4), filtered and concentrated. The pale yellow solid was also washed with cold absolute ethanol (25 mL). 9.05 g of 2,3,5-triiodobenzyl chloride in the form of a white clean solid was obtained in 90% yield.

Workup

  1. extractionThe resulting aqueous phase was extracted with dichloromethane (2×10 ml)
  2. washThe combined organic extracts were washed with NaHCO3 aq (20 ml) and H2O (20 ml)
  3. dry with materialthen dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washThe pale yellow solid was also washed with cold absolute ethanol (25 mL)

Sources & evidence

ORD record
ord-beb4959a595d43828ccf9a72c7d90e22
Source dataset
uspto-grants-2016_09
Patent number
US09434800B2

Reaction notes

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