Carbon Dioxide → 5-Bromo-2,3-difluoro-4-(trimethylsilyl)benzoic acid

HRID 1879630ノート

反応式

HRID 1879630 の反応式
[Li]CCCC.CC1(C)CCCC(C)(C)N1.[Br:16][C:17]1[C:22]([Si:23]([CH3:26])([CH3:25])[CH3:24])=[C:21]([F:27])[C:20]([F:28])=[CH:19][CH:18]=1.[C:29](=[O:31])=[O:30]>C1COCC1.O>[Br:16][C:17]1[C:22]([Si:23]([CH3:24])([CH3:25])[CH3:26])=[C:21]([F:27])[C:20]([F:28])=[C:19]([CH:18]=1)[C:29]([OH:31])=[O:30]

参加物

7

反応物 4

HCID 280Carbon DioxideHCID 130352,2,6,6-TetramethylpiperidineHCID 23070109(6-Bromo-2,3-difluorophenyl)trimethylsilaneHCID 178418339Butyllithium

生成物 1

HCID 585380595-Bromo-2,3-difluoro-4-(trimethylsilyl)benzoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of n-BuLi (2.0 M in hexanes, 11.1 mL, 22.2 mmol) in anhydrous THF (17 mL) at −78° C. was added drop wise 2,2,6,6-tetramethylpiperidine (3.26 g, 22.1 mmol). After being stirred for 15 minutes, a solution of the product from step A (5.86 g, 22.1 mmol) in THF (20 mL) was added. The reaction mixture was stirred at −78° C. for 2 hours, then dry ice (100 g) was added. The mixture was allowed to stand at room temperature overnight, then it was diluted with water and extracted with EtOAc. The combined organics were dried over MgSO4, filtered, then concentrated to afford the title compound. The material was used directly in the next step without further purification. 1H NMR (500 MHz, CDCl3): δ 7.70 (d, J=4.4 Hz, 1H); 0.44 (s, 9H).

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. waitto stand at room temperature overnight
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a6c8e712035e4145a4b7fd1cc77e887a
出典データセット
uspto-grants-2012_11
特許番号
US08318667B2

反応ノート

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