Toluene → Biphenyl-3-yl-dimethylamine

HRID 1510179Notes

Reaction equation

HRID 1510179 reaction equation
C1COCC1.[C:6]1([Mg]Br)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[N:18]([CH3:20])[CH3:19].C1(C)C=CC=CC=1>CCCCCC>[C:15]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:23]=[CH:22][CH:21]=[C:17]([N:18]([CH3:20])[CH3:19])[CH:16]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 23285N,N-Dimethyl-3-chloroanilineHCID 178418255HCID 178418255, compound

Product 1

HCID 12887384Biphenyl-3-yl-dimethylamineYield 94%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using a THF solution of phenylmagnesium bromide (1.19 mL, 1.01 M, 1.2 mmol) and 3-chloro-N,N-dimethylaniline (155.6 mg, 1.0 mmol) as starting materials, the reaction was performed at a scale of 1.0 mmol at 60° C. for 24 hours in the same manner as in Example 2. After performing silica gel column chromatography (toluene=50 and 100% in hexane), the above compound was obtained as a colorless liquid (0.185 g, yield=94%, purity=>98% (GC analysis)).

Workup

  1. customthe above compound was obtained as a colorless liquid (0.185 g, yield=94%, purity=>98% (GC analysis))

Sources & evidence

ORD record
ord-d32c24b7dbb440ab92469b3eaf049135
Source dataset
uspto-grants-2012_07
Patent number
US08211820B2

Reaction notes

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