Benzoyl chloride → HCID 53888575, compound

HRID 2399582Notes

Reaction equation

HRID 2399582 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]#[CH:16])[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(N(CC)CC)C.[Cu](Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]#[C:16][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 11776TriphenylphosphineHCID 53785538HCID 53785538, compound

Product 1

HCID 53888575HCID 53888575, compound

Reagents, catalysts & solvents 3

HCID 24014Cupric ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

Under a nitrogen blanket and at 90° C., 2 g (9.2 mmol) of the acetylene derivative from Example 1 is added to a mixture of 50 mg of copper(II) chloride, 110 mg of palladium(II) acetate, 380 mg of triphenylphosphine and 2.6 g (18.4 mmol) of benzoyl chloride in 100 ml of triethylamine. After 30 minutes, the mixture is allowed to cool and the solid is filtered off. The filtrate is evaporaed down, and the residue is taken up in methyl tert-butyl ether, washed with water, dried and evaporated down. The residue is stirred with diethyl ether and the precipitated pale brown solid is filtered off. 2.0 g (68%) of compound 26, Table 6, remain. Mp. 89°-94° C.

Workup

  1. temperatureto cool
  2. filtrationthe solid is filtered off
  3. washwashed with water
  4. customdried
  5. customevaporated down
  6. filtrationthe precipitated pale brown solid is filtered off

Sources & evidence

ORD record
ord-80039718d68840cc9de077346c36ae5f
Source dataset
uspto-grants-1995_09
Patent number
US05449809

Reaction notes

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