Sodium Carbonate → (2'-Chloro-biphenyl-2-yl)-acetonitrile

HRID 2169122Notes

Reaction equation

HRID 2169122 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C(O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 296252-Bromobenzyl cyanideHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 86725778(2'-Chloro-biphenyl-2-yl)-acetonitrileYield 84.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of (2-bromophenyl)-acetonitrile (13) (5 g, 25.51 mmol) in a mixture of toluene and ethanol (1:1, 150 mL) was added 2-chloro phenyl boronic acid (14) (6 g, 38.2 mmol) and Na2CO3 (8.1 g, 76.53 mmol) at room temperature. Purging was conducting for 30 min with nitrogen. Then triphenyl phosphine (2.6 g, 10.2 mmol) was added followed by Pd(OAc)2 (0.287 g, 1.27 mmol) and further degassing was conducted for another 10 min. The reaction mixture was heated to reflux for 10 h. After completion of the reaction, the mixture was concentrated under reduced pressure to get a crude product which was purified using a silica column using 2% ethyl acetate in hexane to get (2′-chloro-biphenyl-2-yl)-acetonitrile (15) (4.9 g, 84.36%) as a yellow liquid.

Workup

  1. customPurging
  2. customfurther degassing
  3. waitwas conducted for another 10 min
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux for 10 h
  6. customAfter completion of the reaction
  7. concentrationthe mixture was concentrated under reduced pressure
  8. customto get a crude product which
  9. customwas purified

Sources & evidence

ORD record
ord-e960212be5be40c688cc65558aa7053d
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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