Sodium Iodide → HCID 86712466, compound

HRID 1841861Notes

Reaction equation

HRID 1841861 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[I-:45].[Na+]>ClCCl.O>[I-:45].[C:21]([C:20]1[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[C:25]([S+:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:9]=3[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]2=3)[CH:24]=1)([OH:23])=[O:22]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 74784-Methoxybenzoic AcidHCID 13898Dibenzothiophene sulfoxideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 86712466HCID 86712466, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Dibenzothiophene oxide (57 g, 285 mmol) and 4-methoxybenzoic acid (47.7 g, 314 mmol, 1.1 eq) were suspended in dichloromethane (400 mL) and cooled to 0° C. where Eaton's Reagent (285 mL) was added dropwise. The solution was taken off ice and stirred overnight at r.t. The reaction mixture was cooled back to 0° C. and quenched with the slow addition of water (800 mL), followed by ethyl acetate (500 mL). The precipitate was filtered off and the layers separated. The aqueous layer was extracted with ethyl acetate (2×500 mL) and the combined organic layers were washed with water (500 mL). Sodium iodide (341.6 g, 2.28 mol, 4 eq) in water (500 mL) was slowly poured onto the combined aqueous layers. Additional water was slowly added until precipitation of a viscous oil stopped. The crude oil was recrystallized from acetone afford the title compound (72.0 g, 55%) as a white solid. 1H NMR (300 MHz, (d-DMSO) δ: 12.0-13.0 (brs, 1H), 8.54 (d, J=7.8 Hz, 2H), 8.35 (d, J=8.1 Hz, 2H), 8.21 (dd, J=8.7, 2.1 Hz, 1H), 7.99 (t, J=7.8 Hz, 2H), 7.79 (t, J=7.8 Hz, 2H), 7.51 (d, J=8.7 Hz, 1H), 7.44 (d, J=2.1 Hz, 1H), 4.08 (s, 3H).

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was cooled back to 0° C.
  3. customquenched with the slow addition of water (800 mL)
  4. filtrationThe precipitate was filtered off
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with ethyl acetate (2×500 mL)
  7. washthe combined organic layers were washed with water (500 mL)
  8. customThe crude oil was recrystallized from acetone

Sources & evidence

ORD record
ord-4bd13ddb58424a6caab841109a7d001e
Source dataset
uspto-grants-2015_02
Patent number
US08945814B2

Reaction notes

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