Hydrochloric Acid → 6''Fluoro-2-benzyloxy-[1,1':2',1'']terphenyl-3''-carboxylic acid

HRID 269591

반응식

HRID 269591 반응식
[C:1]1([CH2:7][O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[F:34])[C:28]([OH:30])=[O:29].C(=O)([O-])[O-].[K+].[K+].Cl>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[F:34][C:33]1[C:32]([C:16]2[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 705093-Bromo-4-fluorobenzoic acidHCID 587309902'-Benzyloxy-biphenyl-2-boronic acid

생성물 1

HCID 445816556''Fluoro-2-benzyloxy-[1,1':2',1'']terphenyl-3''-carboxylic acid

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

{2′-[(phenylmethyl)oxy]-2-biphenylyl}boronic acid (60 mg, 0.19 mmol) and 3-bromo-4-fluorobenzoic acid (69 mg, 0.31 mmol) were dissolved in 1:1 toluene:ethanol (6 ml) under nitrogen. Potassium carbonate (290 mg, 2.1 mmol) and tetrakis(triphenylphosphine)palladium(0) (23 mg, 0.019 mmol) were added and the mixture heated at 90° C. for 1 h. After cooling, the reaction mixture was poured into water, acidified with 1M HCl solution and extracted with ethyl acetate (15×2 ml), the combined organic layer were dried and evaporated. The residue was then purified on an SPE column using 40% of ethyl acetate in iso-hexane to give the title compound as white solid.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (15×2 ml)
  3. customthe combined organic layer were dried
  4. customevaporated
  5. customThe residue was then purified on an SPE column

출처 및 근거

ORD 기록
ord-87b199b644b94a979230c2456be54945
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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