Triethylamine → Methyl 3-chloro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

HRID 746768Notes

Reaction equation

HRID 746768 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[Cl:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]=1O)[C:20]([O:22][CH3:23])=[O:21].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.CCCCCC>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:26]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:17]([Cl:16])[CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 21841505Methyl 3-chloro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Add dropwise triflic anhydride (6.7 ml, 39.8 mmol) to a solution of methyl 3-chloro-4-hydroxybenzoate (5.42 g, 29.0 mmol), DMAP (490 mg, 4.0 mmol) and triethylamine (5.6 ml, 40.1 mmol) in anhydrous dichloromethane (200 ml). Stir the mixture at room temperature overnight under nitrogen atmosphere. Quench the mixture by addition of a saturated aq. solution of ammonium chloride. Separate the organic layer and extract the aqueous layer with dichloromethane (×3). Wash the combined organic layers with saturated aq. sodium chloride, dry over anhydrous sodium sulfate, filter and concentrate to yield a crude brown oil. Take up this crude oil in hexane and wash the organic layer with water (×3), dry over anhydrous sodium sulfate, filter and concentrate to. yield the title compound.

Workup

  1. customQuench the mixture
  2. additionby addition of a saturated aq. solution of ammonium chloride
  3. customSeparate the organic layer
  4. extractionextract the aqueous layer with dichloromethane (×3)
  5. washWash the combined organic layers with saturated aq. sodium chloride
  6. dry with materialdry over anhydrous sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto yield a crude brown oil
  10. washwash the organic layer with water (×3)
  11. dry with materialdry over anhydrous sodium sulfate
  12. filtrationfilter
  13. concentrationconcentrate to

Sources & evidence

ORD record
ord-12cb95a34db04664bd685eaa8712cbce
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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