Water → HCID 22972067, compound

HRID 1367803Notes

Reaction equation

HRID 1367803 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:25]=[CH:24][N:23]=[C:22]3[C:13]=2[CH:14]=[CH:15][C:16]2[C:21]3=[N:20][CH:19]=[CH:18][C:17]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:8][CH:7]=1.O>C1COCC1.C1(C)C=CC=CC=1>[C:26]1([C:17]2[C:16]3[C:21](=[C:22]4[C:13](=[CH:14][CH:15]=3)[C:12]([C:9]3[CH:8]=[CH:7][CH:6]=[CH:11][CH:10]=3)=[CH:25][C:24]([C:14]3[CH:2]=[C:1]([CH3:4])[CH:3]=[CH:22][CH:13]=3)=[N:23]4)[N:20]=[C:19]([C:7]3[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][CH:6]=3)[CH:18]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 962WaterHCID 728124,7-Diphenyl-1,10-phenanthrolineHCID 178418306HCID 178418306, compound

Product 1

HCID 22972067HCID 22972067, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 8.8 ml of a 1.7 mol/l t-butyllithium solution (15 mmole) was added dropwise to a solution of 2.55 g of 2-bromo-toluence in 20 ml of THF at 0° C. The resulting mixture was stirred for another 2 hours, and then transferred to a stirred suspension of 1.0 g of bathophenanthroline (3 mmole) in 40 ml of toluene in an ice bath. The resulting deep-red solution was stirred overnight at room temperature, and 10 ml of water was then added. The organic layer was separated, and the aqueous layer was extracted with 30 ml of dicholormethane three times. The combined extracts were stirred with 15 g MnO2 for 2 hours. The mixture then was dried over 15 g of anhydrous MgSO4, filtered, and evaporated to dryness. The clean product was obtained after running chromatography in a silica/CH2Cl2 column with a yield of 75 percent. 1H NMR (500 MHz, CDCl3), ppm: 8.50 (s, 2H), 8.22 (d, J=7.5 Hz, 2H), 8.09 (s, 2H), 7.80 (s, 2H), 7.63-7.48 (m, 10H), 7.45 (dd, J=7.0, 7.0 Hz, 2H), 7.31 (d, J=7.0 Hz, 2H), 2.54 (s, 6H). Analysis for m-TBP. Found: C, 88.29, H, 5.40, N, 5.57. Calculated: C, 89.03, H, 5.51, N, 5.46.

Workup

  1. stirringThe resulting deep-red solution was stirred overnight at room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 30 ml of dicholormethane three times
  4. stirringThe combined extracts were stirred with 15 g MnO2 for 2 hours
  5. dry with materialThe mixture then was dried over 15 g of anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe clean product was obtained

Sources & evidence

ORD record
ord-6e088d132e814abe96bdbecb3650ec8f
Source dataset
uspto-grants-2011_02
Patent number
US07893352B2

Reaction notes

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