Sodium Carbonate → Dimethyl 4'-cyanobiphenyl-3,5-dicarboxylate

HRID 1663416Notes

Reaction equation

HRID 1663416 reaction equation
I[C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17].C([O-])([O-])=O.[Na+].[Na+]>CO.[Pd]>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:11]=2)=[CH:20][CH:19]=1)#[N:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 2758568Dimethyl 5-iodoisophthalate

Product 1

HCID 57513453Dimethyl 4'-cyanobiphenyl-3,5-dicarboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of dimethyl 5-iodoisophthalate (6 g, 18.75 mmol, 1 eq.), 4-cyanophenylboronic acid (2.95 g, 19.68 mmol, 1.05 eq.) and Na2CO3 (7.95 g, 74.98 mmol, 4 eq.) in 400 mL of MeOH was degassed by 4 thaw-freeze-pump cycles. Then 1.3 g of 5% Pd/C was added and nitrogen gas was bubbled through the solution for 10 min. The reaction under stirring was carried out at 80° C. for 1 h. Then, the mixture was filtered and washed with EtOH and CH2Cl2. All organic solvents were removed under vacuum and aqueous layer was extracted 4 times with CH2Cl2, the recombined organic layer were washed once with H2O, dried over MgSO4, filtered and evaporated under vacuum. An off-white solid was obtained with 85% yield.

Workup

  1. customnitrogen gas was bubbled through the solution for 10 min
  2. customThe reaction
  3. filtrationThen, the mixture was filtered
  4. washwashed with EtOH and CH2Cl2
  5. customAll organic solvents were removed under vacuum and aqueous layer
  6. extractionwas extracted 4 times with CH2Cl2
  7. washthe recombined organic layer were washed once with H2O
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customAn off-white solid was obtained with 85% yield

Sources & evidence

ORD record
ord-a90777df8bc84225a54165619fa8c8f4
Source dataset
uspto-grants-2011_10
Patent number
US08034952B2

Reaction notes

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