Hydrochloric Acid → 2,3-Dimethyl-4-nitrophenyl trifluoromethanesulfonate

HRID 731673Notes

Reaction equation

HRID 731673 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].[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:19][C:18]=1O.C(N(CC)CC)C.Cl>ClCCl>[CH3:16][C:17]1[C:22]([CH3:23])=[C:21]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:19][C:18]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 133312452,3-Dimethyl-4-nitrophenol

Product 1

HCID 229333962,3-Dimethyl-4-nitrophenyl trifluoromethanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (1.57 mL, 8.77 mmol) was added to 2,3-dimethyl-4-nitrophenol (1.12 g, 6.70 mmol) and triethylamine (2.5 mL, 17.9 mmol) in dichloromethane (40 mL) at 0° C. under Ar atmosphere and the resulting mixture was allowed to stir overnight at r.t. 2M HCl (50 mL) was then added and the solution was extracted with dichloromethane (3×100 mL). The organic extracts were combined, washed with saturated aqueous NaHCO3 (100 mL), diluted with n-heptane (200 mL), and passed through a pad of silica gel to give 1.96 g (98%) of 195JP07 as a yellow oil.

Workup

  1. extractionthe solution was extracted with dichloromethane (3×100 mL)
  2. washwashed with saturated aqueous NaHCO3 (100 mL)
  3. additiondiluted with n-heptane (200 mL)

Sources & evidence

ORD record
ord-32cd6151b84e49519071241f41ec0503
Source dataset
uspto-grants-2009_09
Patent number
US07585877B2

Reaction notes

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