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

HRID 1879630

반응식

HRID 1879630 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a6c8e712035e4145a4b7fd1cc77e887a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318667B2

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