Hydrochloric Acid → 3-Fluoro-4-(methylsulphonyl)benzeneboronic acid

HRID 748883Notes

Reaction equation

HRID 748883 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([B:12]2[O:16]C(C)(C)C(C)(C)[O:13]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].O1CCCC1.O.Cl>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([B:12]([OH:16])[OH:13])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 593927762-(3-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 459336283-Fluoro-4-(methylsulphonyl)benzeneboronic acidYield 42.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Combine 2-(3-fluoro-4-methanesulfonyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (222 mg, 0.74 mmol), NaIO4 (474 mg, 2.2 mmol), tetrahydrofuran (THF, 4 mL) and water (1 mL). Stir for 2 hours and add 2M HCl in diethyl ether (0.2 mL). Stir another 12 hours and filter away the solid. Wash the filtrate with brine (10 mL), dry with MgSO4 and evaporate the solvent. Wash the solid with hexane (2×10 mL) and ether (10 mL). Dry the solid under vacuum to obtain 68 mg of the title compound (42%).

Workup

  1. stirringStir another 12 hours
  2. filtrationfilter away the solid
  3. washWash the filtrate with brine (10 mL)
  4. dry with materialdry with MgSO4
  5. customevaporate the solvent
  6. washWash the solid with hexane (2×10 mL) and ether (10 mL)
  7. customDry the solid under vacuum

Sources & evidence

ORD record
ord-88cf3d67274c4d4d9412231e8da86a7c
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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