Ethyl Acetate → HCID 9855722, compound

HRID 1070408Notes

Reaction equation

HRID 1070408 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Na+].[Na+].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>O1CCOCC1.O>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 4297402-Amino-5-bromobenzonitrile

Product 1

HCID 9855722HCID 9855722, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-amino-5-bromo-benzonitrile (4.0 g, 0.0203 mole) in 55 mL of dioxane was treated with sodium carbonate (7.1 g) in 55 mL of water, phenyl boronic acid (2.72 g, 0.0223 mole), and tetrakistriphenylphosphine palladium (0) (0.235 g). the mixture was heated to 100° C. with stirring under an atmosphere of argon for 3 h., cooled to room temperature, poured into ethyl acetate, washed with 1M HCl, then brine, dried, evaporated and purified by chromatography to give 2.91 g of 4-amino-biphenyl-3-carbonitrile as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with 1M HCl
  3. dry with materialbrine, dried
  4. customevaporated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-46f4fee76a334fdbb4ed966566166e00
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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