Dichloromethane → 1-Methylpyrene

HRID 1914409Notes

Reaction equation

HRID 1914409 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:18]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O>[CH3:18][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 1596271-BromopyreneHCID 574072Trimethylboroxine

Product 1

HCID 169321-MethylpyreneYield 81.7%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixed solution of 7 g of 1-bromopyrene, 6 g of trimethylboroxin, 12 g of cesium carbonate, 2 g of PdCl2(dppf).CH2Cl2, 80 ml of dimethylformamide and 8 ml of distilled water was heated and stirred under a nitrogen gas stream at 80° C. for 7 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by filtration. The resulting solid was purified by silica gel column chromatography and then vacuum-dried to obtain 4.4 g of 1-methylpyrene.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. customThe resulting solid was purified by silica gel column chromatography
  4. customvacuum-dried

Sources & evidence

ORD record
ord-fff84b02595d430f86599072f696d4b5
Source dataset
uspto-grants-2013_12
Patent number
US08610345B2

Reaction notes

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