Trifluoromethanesulfonic acid → HCID 21182816, compound

HRID 1387066Notes

Reaction equation

HRID 1387066 reaction equation
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:16][C:15]3[C:17]([F:23])=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:14]=3[CH:13]=2)=[CH:8][CH:7]=1)(C)(C)C.C(OC1C=CC(C2SC3C=C(OC)C=CC=3C=2)=CC=1)(C)(C)C.OS(C(F)(F)F)(=O)=O>FC(F)(F)CO>[F:23][C:17]1[C:15]2[S:16][C:12]([C:9]3[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=3)=[CH:13][C:14]=2[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

5

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 21182686HCID 21182686, compoundHCID 21182785HCID 21182785, compound

Product 1

HCID 21182816HCID 21182816, compound

Reagents, catalysts & solvents 1

HCID 64092,2,2-TrifluoroethanolSolvent

Procedure

The mixture of 2-(4-tert-butoxyphenyl)-7-fluoro-6-methoxybenzo[b]thiophene and 2-(4-tert-butoxyphenyl)-6-methoxybenzo[b]thiophene (Part B; 3.12 g) in 45 mL of 2,2,2-trifluorethanol at −5° C. was treated with triflic acid (45 μL, 0.51 mmol). After 1 h, the reaction mixture was partitioned between 1 N NaOH and CH2Cl2 (50 mL each). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2; gradient of 5% to 20% THF in hexanes) to give 859 mg of the title compound as a white powder.

Workup

  1. customthe reaction mixture was partitioned between 1 N NaOH and CH2Cl2 (50 mL each)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (SiO2; gradient of 5% to 20% THF in hexanes)

Sources & evidence

ORD record
ord-44318965fe9c4f8f935fc8c78da6315c
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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