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

HRID 2239197ノート

反応式

HRID 2239197 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

Firstly, 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 refluxed for 5 hours. Next, the reaction solution was cooled to room temperature, added with toluene, and then washed with 1N HCl(aq) and water. The resulting solution was dried with magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Next, the residue was purified by silica-gel column chromatography with heptane as an 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 compound (S1-3) from (S1-1) was 97.7%.

後処理

  1. temperaturerefluxed for 5 hours
  2. washwashed with 1N HCl(aq) and water
  3. dry with materialThe resulting solution was dried with magnesium sulfate
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customNext, the residue was purified by silica-gel column chromatography with heptane as an eluent
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-1d2df6d225004f7ab0890a701284f235
出典データセット
uspto-grants-2010_05
特許番号
US07722783B2

反応ノート

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