Ammonium Acetate → (2-Chloro-4-(2-methoxy-2-oxoethyl)phenyl)boronic acid

HRID 1930108Notes

Reaction equation

HRID 1930108 reaction equation
I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].[Cl:12][C:13]1[CH:14]=[C:15]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:16]=[CH:17][C:18]=1[B:19]1[O:23]C(C)(C)C(C)(C)[O:20]1>CC(C)=O.O>[Cl:12][C:13]1[CH:14]=[C:15]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:16]=[CH:17][C:18]=1[B:19]([OH:20])[OH:23]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 58464478Benzeneacetic acid, 3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester2×

Product 1

HCID 59627663(2-Chloro-4-(2-methoxy-2-oxoethyl)phenyl)boronic acidYield 94%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Sodium periodate (1.967 g, 9.20 mmol) and ammonium acetate (0.709 g, 9.20 mmol) were added to a stirred solution of methyl 2-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (Intermediate 2-7; 0.952 g, 3.07 mmol) in acetone (20 mL) and water (10 mL). The resulting suspension was stirred at ambient temperature for 17 hours. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×250 mL). The organic extracts were combined washed with saturated brine (100 mL), dried over MgSO4, filtered and evaporated to afford 2-chloro-4-(2-methoxy-2-oxoethyl)phenylboronic acid (0.656 g, 94%) as a cream oil which solidified on standing, and was used without further purification.

Workup

  1. extractionextracted with EtOAc (3×250 mL)
  2. washThe organic extracts were combined washed with saturated brine (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c8b9df1d012c476bbd31defd3a9be051
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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