Dimethyl Sulfoxide → 4'-Formyl-[1,1'-biphenyl]-2-carbonitrile

HRID 1609174Notes

Reaction equation

HRID 1609174 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=1)#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[CH:20]=[CH:21][C:22]([CH:25]=[O:26])=[CH:23][CH:24]=1)#[N:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13938962-[4-(Hydroxymethyl)phenyl]benzonitrile

Product 1

HCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 53 ml of oxalyl chloride in 2 l of dichloromethane is cooled to -60°. A solution of 88 ml of dimethyl sulfoxide in 150 ml of dichloromethane is added dropwise at this temperature and the mixture is then stirred for 2 minutes. After this, a solution of 117 g of 2'-cyano-4-hydroxymethyl-biphenyl in 1 l of dichloromethane is added dropwise at -60°. After the addition has ended (after about 5 minutes), the mixture is stirred for 15 minutes. After this, 390 ml of triethylamine are added dropwise. The mixture is stirred at -60° for 2 minutes, then allowed to warm to room temperature and poured onto water. The mixture is extracted with dichloromethane, and the organic phase is washed in succession with dilute hydrochloric acid and brine, dried and concentrated. The residue is suspended in hexane, the suspension is filtered with suction, the filter cake is washed, and the product thus obtained is dried at 60° in a high vacuum (elemental analysis: 80.7% C; 4.5% H; 6.7% N; 7.7% O).

Workup

  1. additionAfter the addition
  2. custom(after about 5 minutes)
  3. stirringthe mixture is stirred for 15 minutes
  4. stirringThe mixture is stirred at -60° for 2 minutes
  5. additionpoured onto water
  6. extractionThe mixture is extracted with dichloromethane
  7. washthe organic phase is washed in succession with dilute hydrochloric acid and brine
  8. customdried
  9. concentrationconcentrated
  10. filtrationthe suspension is filtered with suction
  11. washthe filter cake is washed
  12. customthe product thus obtained
  13. customis dried at 60° in a high vacuum (elemental analysis: 80.7% C; 4.5% H; 6.7% N; 7.7% O)

Sources & evidence

ORD record
ord-5da37d717553404c91acff5695063c1e
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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