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

HRID 2239197Notes

Reaction equation

HRID 2239197 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-1d2df6d225004f7ab0890a701284f235
Source dataset
uspto-grants-2010_05
Patent number
US07722783B2

Reaction notes

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