Triethylamine → 3,5-Dichlorobenzyl methanesulfonate

HRID 23061

Reaction equation

HRID 23061 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH2:5][OH:6].[CH3:11][S:12](Cl)(=[O:14])=[O:13].C(N(CC)CC)C>ClCCl>[CH3:11][S:12]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[C:8]([Cl:10])[CH:7]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 432363,5-Dichlorobenzylic alcohol

Product 1

HCID 224922533,5-Dichlorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.5 g of 3,5-dichlorobenzyl alcohol (Aldrich) in 75 mL of dichloromethane at 0° C. was added 1.8 mL of methane sulfonylchloride followed by 3.5 mL of triethylamine added dropwise. After 2 hours the solution was diluted to 150 mL with dichloromethane, washed with 3N HCl, saturated aqueous NaHCO3 dried with Na2SO4 and the solvents removed to yield the desired 3,5-dichlorobenzyl methanesulfonate as a yellow oil that was used without purification.

Workup

  1. additionadded dropwise
  2. washwashed with 3N HCl, saturated aqueous NaHCO3
  3. dry with materialdried with Na2SO4
  4. customthe solvents removed

Sources & evidence

ORD record
ord-3bb7ab3091df4a35b26ba73d3764a69a
Source dataset
uspto-grants-2005_02
Patent number
US06849650B2

Linked notes

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