2'-Hydroxyacetophenone → (4-(Azetidine-1-carbonyl)phenyl)boronic acid

HRID 589028Notes

Reaction equation

HRID 589028 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CCOC(C)=O>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:12][C:13]([O:15][CH3:16])=[O:14])(=[O:10])[CH3:9]

Participants

6

Reactant 3

HCID 83752'-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 13446028(4-(Azetidine-1-carbonyl)phenyl)boronic acidYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Hydroxyphenyl)ethanone (1.0 g, 7.3 mmol) and methyl bromoacetate (0.70 mL, 7.3 mmol) were combined in acetone (20.0 mL) with potassium carbonate (2.0 g, 15 mmol) and was stirred at room temperature. The reaction mixture was stirred for 18 h, diluted with EtOAc and filtered to remove the solids. The organic layer was concentrated to give the sub-title compound as a clear oil (1.5 g, 100%). LCMS calc. for C11H13O4 (M+H)+: m/z=209.1. found: 209.1.

Workup

  1. stirringThe reaction mixture was stirred for 18 h
  2. filtrationfiltered
  3. customto remove the solids
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-21872038f1a248b5942aa2794bd42f31
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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