Sodium Carbonate → 3-Aminobiphenyl

HRID 2427931Notes

Reaction equation

HRID 2427931 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20]>CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]1([C:17]2[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=2)[NH2:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 66827Phenylboronic Acid

Product 1

HCID 167173-AminobiphenylYield 100%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of phenylboronic acid (10.5 g, 86.4 mmol) in 100 mL of MeOH, Na2CO3 (18.3 g, 172.2 mmol) and 3-bromoaniline (14.9 g, 86.4 mmol) were added sequentially. To the so obtained suspension, Pd(OAc)2 (500 mg, 2.16 mmol) was added and the reaction was heated to reflux of solvent until a black suspension appeared; the suspension was cooled at room temperature, diluted with MeOH and the black precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and the residue was splitted in water and CH2Cl2. The organic phase was dried on Na2CO3 and concentrated under reduced pressure to give 3-phenylaniline as a brown oil (14.6 g, yield 100%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux of solvent until a black suspension
  3. customthe black precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was splitted in water
  6. customThe organic phase was dried on Na2CO3
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebe31ed0f4054d24bcb91fc6f46c539f
Source dataset
uspto-grants-2011_06
Patent number
US07968748B2

Reaction notes

Loading…