Sodium Chloride → 3-(Aminomethyl)biphenyl

HRID 1168037

Reaction equation

HRID 1168037 reaction equation
Cl.Br[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].C(=O)([O-])[O-].[Na+].[Na+].[C:17]1(OB(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[C:17]1([C:3]2[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=2)[CH2:6][NH2:7])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 27603683-(Aminomethyl)biphenylYield 84.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

18.25 g of 3-bromobenzylamine hydrochloride, 17.39 g of sodium carbonate in aqueous solution (120 ml) and 1.90 g of tetrakis(triphenylphosphine)palladium (0) were added to toluene (240 ml) under a nitrogen atmosphere. The resulting solution was mixed with 10.00 g of phenylboric acid in ethanol (120 ml) at room temperature with stirring and refluxed under heating for 2 hours. After the reaction, the reaction solution was cooled to room temperature, poured into saturated aqueous sodium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent to give 11.18 g of crude 3-phenylbenzylamine as a brown viscous liquid.

Workup

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure for removal of the solvent

Sources & evidence

ORD record
ord-3c5f2be8e55849fb8b582c0bf4b5e6ee
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Linked notes

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