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

HRID 1400008노트

반응식

HRID 1400008 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a round-bottomed flask was 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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bf24e822bb864843bbf98dc2b1c0afa0
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906914B2

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