Phenylboronic Acid → 3-Amino-biphenyl-2-carbonitrile

HRID 2036843Notes

Reaction equation

HRID 2036843 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6](Br)[C:3]=1[C:4]#[N:5].CC([O-])=O.[K+].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 517044Potassium AcetateHCID 98130382-Amino-6-bromobenzonitrile

Product 1

HCID 463118033-Amino-biphenyl-2-carbonitrileYield 65,900.602%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2-amino-6-bromobenzonitrile (5 g, 0.025 mmol) in toluene (70 mL) was added KOAc (5 g, 0.05 mmol), phenylboronic acid (4.27 g, 0.035 mmol) and cat. Pd(TPP)2Cl2. The reaction mixture was heated to 115° C. for 16 h. After this time, the reaction mixture was filtered and the volatiles were evaporated to yield as residue. The residue was purified by column chromatography (1% EtOAc in hexanes) to provide 3-aminobiphenyl-2-carbonitrile (3.2 g, 65% yield) as light yellow solid. LCMS Method Z: retention time 3.65 min; [M+]=195.2.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered
  2. customthe volatiles were evaporated
  3. customto yield as residue
  4. customThe residue was purified by column chromatography (1% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4e738036875b4648aa47404a709eefbf
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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