1-Chloro-2,3-difluorobenzene → 2-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 506449

반응식

HRID 506449 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:8]=1[F:14].C(O[B:19]1[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]1)(C)C>C1COCC1.O.C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([B:19]2[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])([CH3:26])[O:20]2)=[C:9]([F:13])[C:8]=1[F:14]

참가 물질

7

반응물 3

HCID 27827621-Chloro-2,3-difluorobenzeneHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339Butyllithium

생성물 1

HCID 569732562-(4-Chloro-2,3-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A 2.5M solution of n-butyllithium (2.69 ml, 6.73 mmol) in hexanes was added dropwise to a solution of 1-chloro-2,3-difluorobenzene (1 g, 6.73 mmol) in THF (25 mL) cooled to −78° C. After 45 min at −78° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.253 g, 6.73 mmol) was added dropwise after which the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was diluted with water and ethyl acetate, and the organic phase was extracted twice with water. The aqueous extracts were combined, acidified with 12N HCl to pH 3, and extracted with ethyl acetate. The organic extract was dried and concentrated under vacuum to yield the title compound as an oil product (0.93 g, 50% yield): 1H NMR (CDCl3) δ 7.42 (m, 1H), 7.17 (m, 1H), 1.37 (s, 12H).

후처리

  1. temperatureto warm to ambient temperature
  2. extractionthe organic phase was extracted twice with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-79eedfe1cdf941cf832d82aed8b2f431
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786044B2

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