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

HRID 1808192Notes

Reaction equation

HRID 1808192 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 yield 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
  7. customevaporated

Sources & evidence

ORD record
ord-c05028a42eac4f0e8244e2c42b8d18ff
Source dataset
uspto-grants-2013_01
Patent number
US08357711B2

Reaction notes

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