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

HRID 1908232ノート

反応式

HRID 1908232 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ff28440e58754c3ba49b096c63878518
出典データセット
uspto-grants-2013_12
特許番号
US08598202B2

反応ノート

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