Sodium Carbonate → 4-Propyl-1-(3-chloro-5-fluorophenyl)benzene

HRID 2041807노트

반응식

HRID 2041807 반응식
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](OB(O)O)=[CH:6][CH:5]=1)[CH2:2][CH3:3].Br[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([Cl:22])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C(O)C.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>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 27362231-Bromo-3-chloro-5-fluorobenzeneHCID 21869456(4-Propylphenoxy)boronic acidHCID 86587398Ethanol toluene water

생성물 1

HCID 593039804-Propyl-1-(3-chloro-5-fluorophenyl)benzene수율 97.7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

At first, 25.8 g of 4-propylphenylboric acid (S1-1), 30.0 g of 1-bromo-3-chloro-5-fluorobenzene (S1-2), 2.5 g of tetrakis(triphenylphosphine)palladium, 50.1 g of sodium carbonate and 700 ml of a mixed solvent of toluene/ethanol/water=3/3/1 (volume ratio) were added into a reactor under nitrogen atmosphere, and then the mixture was refluxed for 5 hours. Next, the reaction solution was cooled to room temperature, added with toluene and then washed with 1N hydrochloric acid and water. Then, the resulting solution was dried over magnesium sulfate and then distilled under reduced pressure to remove the solvent. The residue was purified by silica-gel column chromatography with heptane as eluent and then dried under reduced pressure to obtain 34.8 g of 4-propyl-1-(3-chloro-5-fluorophenyl)benzene (S1-3). The yield of the compound (S1-3) from (S1-1) was 97.7%.

후처리

  1. temperaturethe mixture was refluxed for 5 hours
  2. washwashed with 1N hydrochloric acid and water
  3. dry with materialThen, the resulting solution was dried over magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe residue was purified by silica-gel column chromatography with heptane as eluent
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-a9d848b43920476197e11fd537bfb1fe
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586153B2

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