Trifluoroacetic acid → 3,3-Bis(3-bromophenyl)azetidine

HRID 1429274Notes

Reaction equation

HRID 1429274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=3)[CH2:11][N:10](P(=O)(OCC)OCC)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Br:26])[CH:21]=3)[CH2:9][NH:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58032038Diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate

Product 1

HCID 666303673,3-Bis(3-bromophenyl)azetidineYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of diethyl 3,3-bis(3-bromophenyl)azetidin-1-ylphosphonate (960 mg, 1.9 mmol) in anhydrous dichloromethane (5 mL) under N2 was added TFA (5 mL). The mixture was stirred at 20° C. for 3 h, then concentrated by rotary evaporation. The residue was dissolved in dichloromethane (20 mL) and washed with aq. NaHCO3 (30 mL). The organic layer was dried and concentrated to afford 595 mg of the title compound (1.6 mmol, 85%) as a yellow oil which was used directly to next step without purification. LC/MS: [M+1]=368.

Workup

  1. concentrationconcentrated by rotary evaporation
  2. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  3. washwashed with aq. NaHCO3 (30 mL)
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-11d4c049b7ec4776905a10d64a87aac0
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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