Hydrochloric Acid → Boronic acid, [2-[(methylsulfonyl)methyl]phenyl]-

HRID 2248278Notes

Reaction equation

HRID 2248278 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]([OH:11])[OH:10].[CH3:12][S:13]([O-:15])=[O:14].[Na+].Cl>CN(C=O)C>[CH3:12][S:13]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[B:9]([OH:11])[OH:10])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2733271Sodium methanesulfinateHCID 27732782-Bromomethylphenylboronic acid

Product 1

HCID 14371761Boronic acid, [2-[(methylsulfonyl)methyl]phenyl]-Yield 28.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution in DMF (2.0 ml) of [2-(bromomethyl)phenyl]boronic acid (399 mg) was added in one portion to a stirred slurry of sodium methanesulphinate (200 mg) in DMF (2.0 ml). The mixture was stirred for 2.5 h i nd then poured into 1M hydrochloric acid (100 ml) and extracted with EA (3×50 ml). the combined extracts were dried and evaporated. On standing a solid material precipitated, which was washed with ER to give white crystals of the title compound (115 mg), m.p. 133°-137°. T.l.c. (A) ER:hexane (3:2) Rf 0.51.

Workup

  1. extractionextracted with EA (3×50 ml)
  2. customthe combined extracts were dried
  3. customevaporated
  4. customprecipitated
  5. washwhich was washed with ER

Sources & evidence

ORD record
ord-e0f35a844b4b4a03bd6aa7435c8fc8cc
Source dataset
uspto-grants-1991_08
Patent number
US05039673

Reaction notes

Loading…