Bromobenzene → 3-Aminobiphenyl

HRID 2053226Notes

Reaction equation

HRID 2053226 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:8][C:9]1[CH:10]=[C:11](B(O)O)[CH:12]=[CH:13][CH:14]=1>CCOC(C)=O>[C:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=[CH:13][CH:14]=[C:9]([NH2:8])[CH:10]=1

Participants

4

Reactant 2

HCID 7961BromobenzeneHCID 922693-Aminophenylboronic acid

Product 1

HCID 167173-Aminobiphenyl

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Bromobenzene (300 mg, 1.91 mmol) was coupled to 3-amino-phenylboronic acid (355 mg, 2.29 mmol) using Method E. The crude residue was re-dissolved in EtOAc (8 ml) and washed with saturated NaHCO3 (3×8 ml). The organic layer was extracted with 1.2M HCl (1×8 ml) then basified with 6M NaOH until a white precipitate formed. This was then extracted with EtOAc (3×10 ml). The combined organic layers were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound.

Workup

  1. washwashed with saturated NaHCO3 (3×8 ml)
  2. extractionThe organic layer was extracted with 1.2M HCl (1×8 ml)
  3. customformed
  4. extractionThis was then extracted with EtOAc (3×10 ml)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-cda0ae9915dd479eacd558d774ebac02
Source dataset
uspto-grants-2008_02
Patent number
US07326732B2

Reaction notes

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