Triethylamine → 7-Methoxybenzofuran-3-yl trifluoromethanesulfonate

HRID 1057145Notes

Reaction equation

HRID 1057145 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][O:17][C:18]1[C:26]2[O:25][CH2:24][C:23](=O)[C:22]=2[CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:23]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([O:17][CH3:16])[C:26]=2[O:25][CH:24]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 28181127-Methoxybenzofuran-3(2H)-one

Product 1

HCID 208271337-Methoxybenzofuran-3-yl trifluoromethanesulfonateYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Trifluoromethanesulfonic anhydride (4.6 g, 16.3 mmol) was added dropwise to a solution of 7-methoxybenzofuran-3(2H)-one (1.8 g, 10.9 mmol), triethylamine (2.2 g, 21.8 mmol), and dichloromethane (40 mL) at −20° C. The resulting mixture was stirred at −20° C. for 2 h. The reaction mixture was neutralized with saturated aqueous NaHCO3 (22 mL). The organic layer was separated, washed with water (40 mL) and brine (40 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified on a silica gel column using petroleum ether to afford the title compound as yellow oil (2.3 g, yield 71%). 1H NMR (DMSO-d6, 400 MHz): δ 8.67 (s, 1H), 7.36 (t, 1H), 7.21 (d, 1H), 7.20 (d, 1H), 3.96 (s, 3H).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (40 mL) and brine (40 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-4d20252678344c9caa96707f7986cd18
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

Loading…