Oxygen → 3-(3-Bromophenyl)oxetane

HRID 1918376Notes

Reaction equation

HRID 1918376 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl.N[C@@H]1CC[CH2:26][CH2:25][C@H:24]1[OH:29].O=O>CC(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:25]2[CH2:24][O:29][CH2:26]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 977OxygenHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2734318(3-Bromophenyl)boronic acidHCID 12228412Cyclohexanol, 2-amino-, hydrochloride (1:1), (1R,2R)-

Product 1

HCID 534843193-(3-Bromophenyl)oxetaneYield 939.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4.7 g of 3-bromophenylboronic acid, 219 mg of NiI2, 4.3 g of sodium bis(trimethylsilyl)amide, and 106 mg of trans-2-aminocyclohexanol hydrochloride were added to 14 ml of anhydrous 2-propanol and oxygen removed by passing argon through the mixture for 10 minutes. Then, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added and the mixture kept at 80° C. under microwave irradiation for 50 minutes. The mixture was then evaporated, distributed between 100 ml of water and 100 ml of EA, and the aqueous layer extracted twice using 20 ml of EA each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:4 yielded 1.4 g of the title compound, colorless oil. Rf (EA/HEP 1:4)=0.27

Workup

  1. customremoved
  2. customfor 10 minutes
  3. additionThen, a solution of 2.2 g of 3-iodo-oxetane in 1 ml of anhydrous 2-propanol was added
  4. customthe mixture kept at 80° C. under microwave irradiation for 50 minutes
  5. customThe mixture was then evaporated
  6. extractionthe aqueous layer extracted twice
  7. customThe organic layer was then dried
  8. customevaporated

Sources & evidence

ORD record
ord-107c916212b6456ab6c5ccb9e9c7693d
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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