Hydrochloric Acid → 1-(2-Fluoro-4-nitrophenyl)azetidin-3-ol

HRID 1842993Notes

Reaction equation

HRID 1842993 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].[OH:12][CH:13]1[CH2:16][NH:15][CH2:14]1.Cl>C1COCC1>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:15]1[CH2:16][CH:13]([OH:12])[CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 15142903-Hydroxyazetidine

Product 1

HCID 535516781-(2-Fluoro-4-nitrophenyl)azetidin-3-olYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,2-difluoro-4-nitrobenzene (200 mg, 1.25 mmol, 1 eq) in THF (5 mL) was added TEA (0.26 mL, 1.88 mmol, 1.5 eq) and 3-hydroxyazetidine.HCl (205 mg, 1.88 mmol, 1.5 eq) at RT and refluxed for 24 h. THF was evaporated and the residue was washed with water (10 mL) to obtain 1-(2-fluoro-4-nitrophenyl)azetidin-3-ol (200 mg, 75%) as a solid (TLC: EtOAc/PE (3:7), Rf: 0.30).

Workup

  1. customTHF was evaporated
  2. washthe residue was washed with water (10 mL)

Sources & evidence

ORD record
ord-76eb8056079940bb96bea625c783c5b5
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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