Phenylboronic Acid → 3-Bromo-5-phenylpyridine

HRID 555996

Reaction equation

HRID 555996 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15](Br)[CH:16]=1>COCCOC.C([O-])([O-])=O.[Na+].[Na+]>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[C:15]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:16]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 693693,5-Dibromopyridine

Product 1

HCID 27629043-Bromo-5-phenylpyridine

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Phenylboronic acid (0.618 g, 5.065 mmol) is stirred in a mixture of DME (20 ml) and 2M Na2CO3 for 20 minutes. 3,5-dibromopyridine (1.0 g, 4.221 mmol) is added followed by PdCl2(Ph3P)2 (0.296 g, 0.4221 mmol) and the mixture is heated to 100° C. overnight. The DME layer is removed and is diluted with EtOAc, washing with 5M HCl (2×20 ml) then back extracted with EtOAc (70 ml). The acidic aqueous phase is basified with 6M NaOH (50 ml) and extracted with DCM (3×100 ml). The combined organic extracts are dried over MgSO4, filtered and evaporated to an oil which is stirred in iso-hexanes (15 ml) and the resulting solid is removed washing with a further 10 ml of iso-hexanes. Concentration of the organics in vacuo affords the title compound as a white solid MH+[235.74].

Workup

  1. customThe DME layer is removed
  2. additionis diluted with EtOAc
  3. washwashing with 5M HCl (2×20 ml)
  4. extractionthen back extracted with EtOAc (70 ml)
  5. extractionextracted with DCM (3×100 ml)
  6. dry with materialThe combined organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to an oil which
  9. customthe resulting solid is removed
  10. washwashing with a further 10 ml of iso-hexanes

Sources & evidence

ORD record
ord-d7a4332361df48f0bfc48310d49d6196
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Linked notes

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