Ammonium Chloride → 3-Fluoro-3-(3-iodo-phenyl)-oxetane

HRID 334051Notes

Reaction equation

HRID 334051 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]2(O)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.COCCN(S(F)(F)[F:23])CCOC.[NH4+].[Cl-]>C(Cl)Cl>[F:23][C:8]1([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[CH:3]=2)[CH2:11][O:10][CH2:9]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 866882783-(3-Iodophenyl)-3-oxetanol

Product 1

HCID 866882793-Fluoro-3-(3-iodo-phenyl)-oxetane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 500 mg (1.81 mmol) 3-(3-iodo-phenyl)-oxetan-3-ol in 10.6 mL DCM was added 1.17 mL (2.72 mmol) [bis(2-methoxyethyl)amino]sulfur trifluoride at RT under argon atmosphere. The resulting mixture was stirred for 1 h. The mixture was worked up by adding saturated NH4Cl solution. Phases were separated. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=9/1).

Workup

  1. customPhases were separated
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (PE/EtOAc=9/1)

Sources & evidence

ORD record
ord-5b27e117033a40d8833e78842b3c521f
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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