Sodium Carbonate → HCID 59864214, compound

HRID 1010715Notes

Reaction equation

HRID 1010715 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Br:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].CC#N.O.C(O)(C(F)(F)F)=O>O.C1(C)C=CC=CC=1.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>[Br:13][C:14]1[CH:19]=[C:18]([C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][C:6]=2[C:8]([F:11])([F:10])[F:9])[CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 678524-Bromo-3-(trifluoromethyl)anilineHCID 2734318(3-Bromophenyl)boronic acidHCID 22145617Water TFA acetonitrile

Product 1

HCID 59864214HCID 59864214, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 500 mg of 5-amino-2-bromobenzotrifluoride (Dakwood Products, Inc.), 6.2 mMol 3-bromophenylboronic acid (Aldrich), 70 mg of Pd(PPh3)4 and 5 ml of Na2CO3, 2 M solution in H2O, in 14 ml of toluene is stirred at reflux for 1 our. The mixture obtained is allowed to cool to rt and filtered through a pad of celite. The layers obtained are separated and the aqueous phase obtained is extracted with CH2Cl2. The organic phase obtained is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The concentration residue obtained is subjected to MPLC(CH3CN/H2O/TFA). 3′-Bromo-2-trifluoromethyl-biphenyl-4-amine is obtained. MS: 315.9 [M−1]−; HPLCDtRet=4.9; Rf=0.16 (Hexane/EtOAc, 4:1).

Workup

  1. temperatureat reflux for 1 our
  2. customThe mixture obtained
  3. filtrationfiltered through a pad of celite
  4. customThe layers obtained
  5. customare separated
  6. customthe aqueous phase obtained
  7. extractionis extracted with CH2Cl2
  8. customThe organic phase obtained
  9. washis washed with brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe concentration residue obtained

Sources & evidence

ORD record
ord-3bc38c44f7a7480482f4d26398e71ed0
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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