Trifluoromethanesulfonic anhydride → Trifluoro-methanesulfonic acid 2-chloro-4-isopropyl-phenyl ester

HRID 2264986Notes

Reaction equation

HRID 2264986 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[Cl:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:18]=1O>C(Cl)Cl.N1C=CC=CC=1>[Cl:16][C:17]1[CH:22]=[C:21]([CH:23]([CH3:25])[CH3:24])[CH:20]=[CH:19][C:18]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 126520992-Chloro-4-isopropylphenol

Product 1

HCID 59596633Trifluoro-methanesulfonic acid 2-chloro-4-isopropyl-phenyl esterYield 78.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Trifluoromethanesulfonic anhydride (2.14 g, 7.6 mmol) was dissolved in DCM (5 ml) and cooled to 5° C. To this was added 2-chloro-4-isopropyl-phenol (1.23 g, 7.2 mmol), in 10 ml DCM and 1.75 ml pyridine, dropwise. The reaction mixture was stirred at 110° C. for 2 hours. The resultant dark solution was washed with 1M HCl (20 ml), water (20 ml) and saturated aqueous NaHCO3 (20 ml). The DCM extract was dried and concentrated in vacuo to provide the title compound as a dark orange oil (1.71 g, 78%). 1H NMR (CDCl3) 1.22-1.29 (6H, d, J=6.87 Hz), 2.88-3.00 (1H, sept, J=6.89 Hz), 7.15-7.20 (1H, m), 7.24 (1H, d, J=8.36 Hz), 7.36 (1H, d, J=2.17 Hz).

Workup

  1. washThe resultant dark solution was washed with 1M HCl (20 ml), water (20 ml) and saturated aqueous NaHCO3 (20 ml)
  2. extractionThe DCM extract
  3. customwas dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6366ad55bd634365b777a553a5a9c55b
Source dataset
uspto-grants-2010_12
Patent number
US07855216B2

Reaction notes

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