Trifluoromethanesulfonic acid → HCID 178499542, compound

HRID 625184Notes

Reaction equation

HRID 625184 reaction equation
[OH:1][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[CH:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[S:14](=O)[C:13]=2[CH:12]=[CH:11][CH:10]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(Cl)Cl>[O-:4][S:2]([C:5]([F:8])([F:7])[F:6])(=[O:3])=[O:1].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([SH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21](=[O:23])[C:22]3[C+:9]=[CH:10][CH:11]=[CH:12][C:13]2=3)=[CH:29][C:28]=1[CH2:33][C:34]([O:36][CH3:37])=[O:35]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 99590Methyl 2-methoxybenzeneacetateHCID 31809910lambda~4~-Thioxanthene-9,10-dione

Product 1

HCID 178499542HCID 178499542, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Triflic acid (7.3 mL, 43.4 mmol) was added dropwise to a solution of thioxanthone oxide (5.00 g, 21.7 mmol) and methyl 2-(2-methoxyphenyl)acetate (4.31 g, 23.9 mmol) in DCM (60 mL) at −78° C. and slowly warmed to 25° C. overnight. The reaction mixture was quenched with water (100 mL), the layers separated, and the aqueous phase washed with water (4×100 mL) and concentrated to a crude solid. The crude solid was dissolved in minimal acetone, precipitated into MTBE (1 L), and filtered to afford the title compound (10.0 g, 85%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.66-8.69 (m, 2H), 8.19-8.22 (m, 3H), 8.10-8.13 (m, 4H), 7.91 (d, J=2.5 Hz, 1H), 7.37 (d, J=9 Hz, 1H), 3.96 (s, 3H), 3.61 (s, 2H), 3.57 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. customthe layers separated
  3. washthe aqueous phase washed with water (4×100 mL)
  4. concentrationconcentrated to a crude solid
  5. dissolutionThe crude solid was dissolved in minimal acetone
  6. customprecipitated into MTBE (1 L)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-407f2587f7004a3db987b327ddafadd3
Source dataset
uspto-grants-2016_04
Patent number
US09304394B2

Reaction notes

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