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Potassium Carbonate → [4-Benzyloxy-4'-(trifluoromethoxy)biphenyl-3-yl]acetic acid

HRID 1667636
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HRID 1667636 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:26]2[CH:25]=[CH:24][C:23]([O:22][C:21]([F:20])([F:32])[F:33])=[CH:28][CH:27]=2)=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 33070112-[2-(Benzyloxy)-5-bromophenyl]acetic acid

생성물 1

HCID 24804676[4-Benzyloxy-4'-(trifluoromethoxy)biphenyl-3-yl]acetic acid수율 48.9%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매

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온도
80 °C

실험 절차

A mixture of 2-benzyloxy-5-bromophenylacetic acid (261 mg, 0.813 mmol), 4-(trifluoromethoxy)phenyl boronic acid (218 mg, 1.056 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (43 mg, 0.057 mmol), potassium carbonate (169 mg, 1.22 mmol), dioxane (4 ml) and water (0.5 ml) was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, and the solution was filtered through celite. The residue obtained by concentration of the filtrate under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2) to give the title compound (160 mg, 48.9%) as a white solid.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. filtrationthe solution was filtered through celite
  5. customThe residue obtained by concentration of the filtrate under reduced pressure
  6. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:2)

출처 및 근거

ORD 기록
ord-e4c22962861d4369a18d15a21b4133ec
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044236B2

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