1-Iodoheptane → HCID 11580147, compound

HRID 1243978Notes

Reaction equation

HRID 1243978 reaction equation
[C:1]1([S:7]([CH:10]([F:12])[F:11])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13](I)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].CC([O-])(C)C.[K+]>CN(C=O)C>[C:1]1([S:7]([C:10]([F:12])([F:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 202741-IodoheptaneHCID 11816356((Difluoromethyl)sulfonyl)benzene2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 11580147HCID 11580147, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-50 °C

Procedure

Typical Procedure for Nucleophilic Substitution Reactions of Difluoromethyl Phenyl Sulfone with Alkyl Iodides. Under an argon atmosphere, into a Schlenk flask containing difluoromethyl phenyl sulfone (192 mg, 1 mmol) and n-heptyl iodide (904 mg, 4 mmol) in DMF (4 mL) at −50° C., was added dropwise via a syringe t-BuOK (224 mg, 2 mmol) in DMF (4 mL). The reaction mixture was stirred at −50° C. for 1 h, and the completion of the reaction was monitored by 19F NMR. The reaction was then quenched by adding 1N HCl aqueous solution (5 mL) at −50° C., followed by warming to room temperature. A saturated NaCl aqueous solution (10 mL) was added, and the mixture was extracted with Et2O (15 mL×3). The combined organic phase was dried over MgSO4, filtered, and the solvent was removed in a rotary evaporator. The residue was further purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 1,1-difluorooctyl phenyl sulfone (4a) (230 mg, 79% yield) as a colorless oily liquid. 1H NMR (500 MHz, CDCl3): δ 0.88 (t, J=6.9 Hz, 3 H); 1.28 (m, 8 H); 1.64 (m, 2 H); 2.33 (m, 2H); 7.60 (t, J=8.3 Hz, 2H); 7.73 (t, J=7.3 Hz, 1H); 7.99 (d, J=7.9 Hz, 2H). 13C NMR (125 MHz, CDCl3): δ 13.9; 20.7 (t, J=3.4 Hz); 22.4; 28.7; 29.0; 29.1; 31.4; 124.6 (t, J=286 Hz); 129.1; 130.6; 132.7; 135.1. 19F NMR (470 MHz, CDCl3): δ −104.2 (t, J=19 Hz). GC-MS (EI, m/z): 291 (M++1); 142; 77. HRMS (EI): m/z calcd for C14H21F2O2S (M++H) 291.1230, found 291.1222.

Workup

  1. customThe reaction was then quenched
  2. additionby adding 1N HCl aqueous solution (5 mL) at −50° C.
  3. temperatureby warming to room temperature
  4. additionA saturated NaCl aqueous solution (10 mL) was added
  5. extractionthe mixture was extracted with Et2O (15 mL×3)
  6. dry with materialThe combined organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in a rotary evaporator
  9. customThe residue was further purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-85a6f14c787a4068a2c27daaa3a45437
Source dataset
uspto-grants-2006_10
Patent number
US07119232B2

Reaction notes

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