Triethylamine → Methyl 4-[(pentafluorophenoxy)sulfonyl]benzoate

HRID 401771Notes

Reaction equation

HRID 401771 reaction equation
Cl[S:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:15][C:16]1[C:21]([OH:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=1[F:26].CCN(CC)CC>C(Cl)Cl>[F:15][C:16]1[C:21]([O:22][S:2]([C:5]2[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=2)(=[O:4])=[O:3])=[C:20]([F:23])[C:19]([F:24])=[C:18]([F:25])[C:17]=1[F:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13041PentafluorophenolHCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Product 1

HCID 57732203Methyl 4-[(pentafluorophenoxy)sulfonyl]benzoateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(chlorosulfonyl)benzoate (Preparation 2, 606 mg, 2.1 mmol, 1 eq) in DCM (35 ml) was added pentafluorophenol (412 mg, 2.2 mmol, 1.1 eq) and Et3N (540 mg, 5.4 mmol, 2.5 eq) and the reaction mixture stirred at room temperature until all of the starting material was consumed. The solvent was evaporated in vacuo and the residue redissolved in ethyl acetate (10 ml), washed with water (10 ml), saturated sodium hydrogen carbonate (10 ml), dried over sodium sulphate, filtered and evaporated to yiled the title compound as a white solid (690 mg, 1.8 mmol, 85%).

Workup

  1. customwas consumed
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue redissolved in ethyl acetate (10 ml)
  4. washwashed with water (10 ml), saturated sodium hydrogen carbonate (10 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-8905d3e4bf1f49d8ab52f4426af64513
Source dataset
uspto-grants-2014_06
Patent number
US08741934B2

Reaction notes

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