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

HRID 1262186Notes

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

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) was stirred at 40° C. for 18 hours. The mixture was cooled to room temperature and the volatiles were evaporated. The residue was suspended in saturated aqueous ammonium chloride (100 mL). The aqueous phase was decanted from the waxy solid, rinsed with water (50 mL), and decanted again. The waxy solid was dissolved in methanol (50 mL), filtered to remove insoluble salts and evaporated to obtain 4-[(4-boronophenyl)methyl]-thiomorpholine 1,1-dioxide as a tan foam (2.48 g). The recovered material was crude by 1HNMR but was used without further purification.

Workup

temperatureThe mixture was cooled to room temperature
customthe volatiles were evaporated
customThe aqueous phase was decanted from the waxy solid
washrinsed with water (50 mL)
customdecanted again
dissolutionThe waxy solid was dissolved in methanol (50 mL)
filtrationfiltered
customto remove insoluble salts
customevaporated

Sources & evidence

ORD record: ord-8ceeefd2ff06415c9579861efdd54dcd
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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