Ethyl Acetate → 1-[3-(5-Bromo-2-hydroxy-benzyl)-azetidin-1-yl]-2,2,2-trifluoro-ethanone

HRID 237301Notes

Reaction equation

HRID 237301 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:19]C)=[C:6]([CH:18]=1)[CH2:7][CH:8]1[CH2:11][N:10]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:9]1.B(Br)(Br)Br.C([O-])(O)=O.[Na+].CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([CH:18]=1)[CH2:7][CH:8]1[CH2:11][N:10]([C:12](=[O:17])[C:13]([F:15])([F:16])[F:14])[CH2:9]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 584051591-[3-(5-Bromo-2-methoxy-benzyl)-azetidin-1-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 584051121-[3-(5-Bromo-2-hydroxy-benzyl)-azetidin-1-yl]-2,2,2-trifluoro-ethanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[3-(5-bromo-2-methoxy-benzyl)-azetidin-1-yl]-2,2,2-trifluoro-ethanone (66 mg, 0.19 mmol) in dry DCM (10 mL) at 0° C. was added BBr3 (1.0 M in DCM, 370 mL, 0.37 mmol). After warming to rt overnight, saturated NaHCO3 solution and EtOAc were added. The aqueous portion was extracted twice with EtOAc and the combined organic extracts were dried (Na2SO4) and concentrated to provide the title compound (59 mg, 92%). MS (ESI): mass calcd. for C12H11BrF3NO2, 337.0; m/z found, 338.0 [M+H]+. 1H NMR (CDCl3): 7.23-7.10 (m, 2H), 6.70 (t, J=8.7 Hz, 1H), 4.53-4.40 (m, 1H), 4.27-4.11 (m, 2H), 3.97 (dd, J=10.7, 6.0 Hz, 1H), 3.17-3.01 (m, 1H), 3.01-2.78 (m, 2H).

Workup

  1. extractionThe aqueous portion was extracted twice with EtOAc
  2. dry with materialthe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1155c6161b9423b807f81e10dbb75e1
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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