Benzene, 1,3-diiodo- → 3-(3-Iodophenyl)-3-oxetanol

HRID 334050

Reaction equation

HRID 334050 reaction equation
C([Li])CCC.I[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([I:13])[CH:8]=1.[O:14]1[CH2:17][C:16](=[O:18])[CH2:15]1.[NH4+].[Cl-]>C1COCC1>[I:13][C:9]1[CH:8]=[C:7]([C:16]2([OH:18])[CH2:17][O:14][CH2:15]2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 12270Benzene, 1,3-diiodo-HCID 25517Ammonium ChlorideHCID 150242543-OxetanoneHCID 178418339Butyllithium

Product 1

HCID 866882783-(3-Iodophenyl)-3-oxetanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.55 mL (6.37 mmol) n-butyl lithium (2.5 M in THF) was added dropwise to a mixture of 2.00 g (6.06 mmol) 1,3-diiodobenzene in 40 mL THF under argon atmosphere at −70° C. The resulting mixture was stirred for 15 min 476 μL (7.28 mmol) 3-oxetanone was added and the mixture was stirred over night at RT. The mixture was worked up by adding saturated NH4Cl solution followed by extraction with EtOAc. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by HPLC.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by HPLC

Sources & evidence

ORD record
ord-318a8a5cad21415f8162d4a86d0ffd30
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Linked notes

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