Sodium Carbonate → 2,3',4',5'-Tetrafluorobiphenyl-4-ol

HRID 2041808노트

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HRID 2041808 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](OB(O)O)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.O>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.C1(C)C=CC=CC=1>[F:9][C:3]1[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=1[C:13]1[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27791534-Bromo-3-fluorophenolHCID 18180031Water 1,2-dimethoxyethaneHCID 21870694HCID 21870694, 화합물

생성물 1

HCID 210521442,3',4',5'-Tetrafluorobiphenyl-4-ol수율 81.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

At first, 75.0 g of 4-bromo-3-fluorophenol (S3-1), 82.9 g of 3,4,5-trifluorophenyl-boric acid (S3-2), 13.6 g of tetrakis(triphenylphosphine)palladium, 108.5 g of sodium carbonate and 1100 ml of a mixed solvent of dimethoxyethane/water=2/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and the mixture was heated to 80° C. and stirred for 4 hr. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Afterwards, the solution was dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. Subsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent and then dried under reduced pressure. The obtained residue was recrystallized in heptane to obtain 77.5 g of 3-fluoro-4-(3,4,5-trifluorophenyl)phenol (S3-3). The yield of (S3-3) from (S3-1) was 81.5%.

후처리

  1. temperatureNext, the reaction solution was cooled to room temperature
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialAfterwards, the solution was dried over magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customSubsequently, the product was purified by silica-gel column chromatography with a mixed solvent of heptane/ethyl acetate=4/1 as the eluent
  7. customdried under reduced pressure
  8. customThe obtained residue was recrystallized in heptane

출처 및 근거

ORD 기록
ord-30105a1425ba4ee4aaf6db7ac644bc8e
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586153B2

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