Toluene → Benzophenone

HRID 1181161Notes

Reaction equation

HRID 1181161 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8](N)(N)[CH2:9][CH2:10][CH2:11][CH3:12].C([O:17][CH2:18][CH3:19])C>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.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.[Fe+2]>[C:18]([C:19]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:17])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 21872002Pentane-1,1-diamineHCID 178506046HCID 178506046, compound

Product 1

HCID 3102BenzophenoneYield 21%

Reagents, catalysts & solvents 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst

Conditions

Temperature
90 °C

Procedure

A dried Schlenk tube was charged with methyl 4-(p-bromobenzoyl) benzoate (6) (0.20 g, 0.63 mmol), tris (dibenzylidene acetone) dipalladium (0.029 g, 0.032 mmol), DPPF (0.035 g, 0.063 mmol) and toluene (8 mL) under nitrogen. The reaction was capped with a polytetrafluoroethylene (PTFE) septum, and pentanediamine (0.026 g, 0.252 mmol) was added via syringe. The reaction mixture was then heated to 90° C. for 12 hours. The cooled mixture was diluted with diethyl ether (30 mL) and then concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether/ethyl acetate, 50/50, v/v) afforded 0.072 grams (a yield of 21%) as a pale yellow solid:

Workup

  1. additionwas added via syringe
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography on silica gel (petroleum ether/ethyl acetate, 50/50
  4. customv/v) afforded 0.072 grams (a yield of 21%) as a pale yellow solid

Sources & evidence

ORD record
ord-fa5162fa27e54ebb983a54afb039f4fe
Source dataset
uspto-grants-2007_10
Patent number
US07285363B2

Reaction notes

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