Hydrochloric Acid → {4-[(Trifluoromethyl)sulfanyl]phenyl}boronic acid

HRID 1908232Notes

Reaction equation

HRID 1908232 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([S:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[O:3]1.I([O-])(=O)(=O)=O.[Na+].Cl>C1COCC1.O>[F:19][C:16]([S:15][C:12]1[CH:11]=[CH:10][C:9]([B:4]([OH:5])[OH:3])=[CH:14][CH:13]=1)([F:18])[F:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 451588394,4,5,5-Tetramethyl-2-{4-[(trifluoromethyl)sulfanyl]phenyl}-1,3,2-dioxaborolane

Product 1

HCID 46739571{4-[(Trifluoromethyl)sulfanyl]phenyl}boronic acidYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a round-bottomed flask were added 4,4,5,5-tetramethyl-2-(4-trifluoromethylsulfanyl-phenyl)-[1,3,2]dioxaborolane (960 mg, 3.16 mmol) and sodium periodate (2.03 g, 9.48 mmol) in THF and water (4:1, 26 mL). The resulting suspension was stirred at rt for 30 min. HCl (1 N aq., 2.21 mL) was added to the suspension and the reaction mixture was stirred at rt for 18 h. The resulting precipitate was removed by filtration and washed with hexanes. The filtrate was diluted with water (25 mL) and extracted with EtOAc (25 mL). The aqueous layer was extracted with EtOAc (10 mL×2), and the combined organic layers dried (Na2SO4) and concentrated to yield the title compound (512 mg, 73%).

Workup

  1. stirringthe reaction mixture was stirred at rt for 18 h
  2. customThe resulting precipitate was removed by filtration
  3. washwashed with hexanes
  4. additionThe filtrate was diluted with water (25 mL)
  5. extractionextracted with EtOAc (25 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (10 mL×2)
  7. dry with materialthe combined organic layers dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ff28440e58754c3ba49b096c63878518
Source dataset
uspto-grants-2013_12
Patent number
US08598202B2

Reaction notes

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