Bromobenzene → 1-Phenylazetidin-3-ol

HRID 237291Notes

Reaction equation

HRID 237291 reaction equation
[NH:1]1[CH2:4][CH:3]([OH:5])[CH2:2]1.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:7]1([N:1]2[CH2:4][CH:3]([OH:5])[CH2:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 15142903-HydroxyazetidineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 224365261-Phenylazetidin-3-olYield 5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of azetidin-3-ol (2 mmol), bromobenzene (2 mmol), Pd(OAc)2 (0.1 mmol), 2-(di-tert-butylphosphino)biphenyl (0.2 mmol) and NaOtBu (3 mmol) in toluene (3 mL) was heated at 100° C. for 1 h. The mixture was cooled to rt and purified via PTLC providing the title compound (15 mg).

Workup

  1. temperatureThe mixture was cooled to rt
  2. custompurified via PTLC

Sources & evidence

ORD record
ord-651552fdec994a6aabf55f5a2157ea67
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

Loading…