Benzonitrile → Tritylamine

HRID 1464634Notes

Reaction equation

HRID 1464634 reaction equation
O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([Li])CCC.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:31](#[N:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>O1CCCC1>[C:12]1([C:31]([NH2:38])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 7505BenzonitrileHCID 7961BromobenzeneHCID 21585214Cerium trichloride heptahydrateHCID 178418339ButyllithiumHCID 178506676HCID 178506676, compound

Product 1

HCID 138598TritylamineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Cerium chloride heptahydrate (15.0 g, 40 mmol) was dried and stirred with 80 mL of dry tetrahydrofuran as described in Example 1. To this was added by cannulation below -50° a solution of phenyllithium prepared by addition of 16 mL of 2.5M n-butyllithium in hexanes (40 mmol) to 6.28 g (40 mmol) of bromobenzene in 15 mL of tetrahydrofuran below -40°. The mixture was stirred in a dry ice-acetone bath for 30 minutes, and 1.34 g (13 mmol) of benzonitrile in 2 mL of tetrahydrofuran were added. The bath was removed and the mixture was stirred for 2 hours. Isolation as described in Example 1 gave 3.30 g (98%) of triphenylmethylamine, identical by infrared, 1H and 13C NMR spectroscopy with an authentic sample.

Workup

  1. customThe bath was removed
  2. stirringthe mixture was stirred for 2 hours

Sources & evidence

ORD record
ord-607324ea450645c0ab1d6c23a5597ec5
Source dataset
uspto-grants-1994_04
Patent number
US05306821

Reaction notes

Loading…