Hydrochloric Acid → 1-(2-Fluorobiphenyl-4-yl)cyclopropanecarboxylic acid

HRID 1444850노트

반응식

HRID 1444850 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[F:14].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:3]1[CH:4]=[C:5]([C:8]2([C:11]([OH:13])=[O:12])[CH2:10][CH2:9]2)[CH:6]=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 116518041-(4-Bromo-3-fluorophenyl)cyclopropane-1-carboxylic acid

생성물 1

HCID 117086541-(2-Fluorobiphenyl-4-yl)cyclopropanecarboxylic acid수율 214%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매

반응 조건

온도
130 °C

실험 절차

800 mg (3.1 mmoles) of 4-bromo-3-fluorophenylcyclopropanecarboxylic acid and 650 mg (3.4 mmoles) of phenylboronic acid are suspended in 8 ml of a 2M K2CO3 aqueous solution. The mixture is added with tetrabutylammonium bromide (960 mg, 3 mmoles) and palladium(II) acetate (40 mg, 0.18 mmoles) and heated at 130° C. in a closed reactor for 30 minutes. After cooling at room temperature, the mixture is added with 2M HCl (25 ml) and extracted with ethyl acetate. The organic phase is washed with 1N HCl, then with brine, finally dried and concentrated under vacuum to give an oil (1.7 g), which is crystallized from isopropyl ether-hexane to afford the product as a white solid (0.2 g).

후처리

  1. temperatureAfter cooling at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 1N HCl
  4. dry with materialwith brine, finally dried
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-3479cbd68c3a42028a4ec291cb975532
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662995B2

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