HCID 135979345, compound → HCID 178424794, compound

HRID 1689832Notes

Reaction equation

HRID 1689832 reaction equation
[CH2:1]([Hf:8](CC1C=CC=CC=1)(CC1C=CC=CC=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=[C:36]([C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[C:47]([NH:54][C:55]4[C:60]([CH3:61])=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:62])[CH:48]=[CH:49][CH:50]=3)[N:45]=2)[C:35]=1[OH:63])([CH3:33])([CH3:32])[CH3:31]>C1(C)C=CC=CC=1>[C:30]([C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=[C:36]([C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[C:47]([NH:54][C:55]4[C:60]([CH3:61])=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:62])[CH:48]=[CH:49][CH:50]=3)[N:45]=2)[C:35]=1[O-:63])([CH3:31])([CH3:32])[CH3:33].[CH2:9]([Hf+2:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:30]([C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:37]=[C:36]([C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[C:47]([NH:54][C:55]4[C:60]([CH3:61])=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:62])[CH:48]=[CH:49][CH:50]=3)[N:45]=2)[C:35]=1[O-:63])([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 135979345HCID 135979345, compoundHCID 178420296HCID 178420296, compound

Product 1

HCID 178424794HCID 178424794, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of tetrabenzylhafnium (0.47 g, 0.86 mmol) in toluene (5 mL) is added at 0° C. to a solution of 2,4-di-tert-butyl-6-[8-(2,6-dimethylanilino)-2-quinolinyl]phenol (0.30 g, 0.66 mmol) in toluene (10 mL). The color of the mixture changes from pale yellow to yellow-orange. The resulting mixture is allowed to warm to room temperature and is then stirred for 8 days at 40° C. The mixture is evaporated, and pentane (20 mL) is added. The crystalline precipitate is separated by decantation, washed with pentane, and dried in vacuo. Yield of 34, a yellow crystalline powder: 0.26 g (48%). 1H NMR (C6D6) δ: 7.74-7.66 (m, 3H); 7.45 (d, 1H); 7.22 (d, 1H); 7.15-7.13 (m, 3H); 6.99 (t, 1H); 6.79-6.62 (m, 10H); 6.18 (d, 1H); 2.40 (d, 2H); 2.31 (s, 6H); 1.97 (d, 2H); 1.75 (s, 9H); 1.36 (s, 9H).

Workup

  1. customThe mixture is evaporated
  2. additionpentane (20 mL) is added
  3. customThe crystalline precipitate is separated by decantation
  4. washwashed with pentane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ebbc615bf4b84cfeb12b03fcc525f0f0
Source dataset
uspto-grants-2012_04
Patent number
US08153544B2

Reaction notes

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