Dimethylformamide → 5-Hydroxy[1,1'-biphenyl]-3-carbonitrile

HRID 1820696Notes

Reaction equation

HRID 1820696 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:14])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.CCCCCCC.[CH3:22][N:23](C=O)C>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.[C-]#N.[Zn+2].[C-]#N>[OH:14][C:4]1[CH:3]=[C:2]([C:22]#[N:23])[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8900HeptaneHCID 156614915-Bromo[1,1'-biphenyl]-3-ol

Product 1

HCID 532198065-Hydroxy[1,1'-biphenyl]-3-carbonitrileYield 38%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
200 °C

Procedure

Tetrakis(triphenylphosphine)palladium (0) (116 mg, 0.1 mmol) was added to 5-bromobiphenyl-3-ol (250 mg, 1 mmol) and zinc cyanide (117 mg, 1.0 mmol) dissolved in DMF (5 mL) in a microwave vessel. The reaction vessel was sealed and then heated at 200° C. for 300 seconds. The reaction was quenched with water and the product was extracted into DCM. The solution was filtered and then concentrated in vacuo. The crude material was then purified by chromatography on silica gel. Elution with 10:90 ethyl acetate:heptane afforded 5-hydroxybiphenyl-3-carbonitrile (74 mg, 0.379 mmol, 38%). M.S. (ESI) (m/z): 194 [M−H]−.

Workup

  1. customThe reaction vessel was sealed
  2. customThe reaction was quenched with water
  3. extractionthe product was extracted into DCM
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was then purified by chromatography on silica gel
  7. washElution with 10:90 ethyl acetate

Sources & evidence

ORD record
ord-d5c640413d154d00a681e15086ef369d
Source dataset
uspto-grants-2009_10
Patent number
US07605170B2

Reaction notes

Loading…