Acetone → (4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid

HRID 472337Notes

Reaction equation

HRID 472337 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([B:9]([OH:11])[OH:10])=[CH:5][CH:4]=1.[NH:12]1[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CC(C)=O>>[B:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]2[CH2:17][CH2:16][S:15](=[O:19])(=[O:18])[CH2:14][CH2:13]2)=[CH:4][CH:5]=1)([OH:11])[OH:10]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 27355934-(Bromomethyl)phenylboronic acidHCID 6484228Thiomorpholine 1,1-dioxide

Product 1

HCID 54970580(4-((1,1-Dioxidothiomorpholino)methyl)phenyl)boronic acid

Conditions

Temperature
40 °C

Procedure

A suspension of (4-bromomethylphenyl)boronic acid (2.00 g, 9.31 mmol), thiomorpholine 1,1-dioxide (1.50 g, 11.1 mmol) and potassium carbonate (2.60 g, 18.8 mmol) in acetone (25 mL, 340 mmol) was heated at 40° C. for 18 hours then cooled to room temperature. The volatiles were evaporated and the residue was suspended in saturated aqueous ammonium chloride (100 mL). The aqueous was decanted from the waxy solid and the solid was dissolved in methanol (50 mL), filtered to remove insoluble salts and evaporated. 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide was isolated as a tan foam. The crude material was used without further purification.

Workup

  1. temperaturethen cooled to room temperature
  2. customThe volatiles were evaporated
  3. customThe aqueous was decanted from the waxy solid
  4. dissolutionthe solid was dissolved in methanol (50 mL)
  5. filtrationfiltered
  6. customto remove insoluble salts
  7. customevaporated

Sources & evidence

ORD record
ord-b976641f55424446aab7a54ccbcf9797
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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