(Diethylamino)sulfur trifluoride → 3-(4-Bromophenyl)-3-fluorooxetane

HRID 385722Notes

Reaction equation

HRID 385722 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.CCN(S(F)(F)[F:19])CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([F:19])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 583823793-(4-Bromophenyl)oxetan-3-ol

Product 1

HCID 595256233-(4-Bromophenyl)-3-fluorooxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

3-(4-Bromophenyl)oxetan-3-ol (1.55 g, 6.77 mmol) was taken up in DCM (100 mL) and cooled to −78° C. DAST (1.073 mL, 8.12 mmol) was added and the mixture was stirred at −78° C. for 90 minutes followed by 0° C. for 20 minutes. Saturated NaHCO3 was added and the products extracted into DCM (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes) gave the title compound as a yellow oil.

Workup

  1. waitfollowed by 0° C. for 20 minutes
  2. extractionthe products extracted into DCM (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash silica gel column chromatography (0-10% EtOAc-hexanes)

Sources & evidence

ORD record
ord-868f88ee52db49e3b56337e79c238a3f
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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