Pyridine → [1,1'-Biphenyl]-2-carbonyl chloride

HRID 2418798Notes

Reaction equation

HRID 2418798 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7](O)=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.N1C=CC=CC=1.S(Cl)([Cl:24])=O>C1(C)C=CC=CC=1>[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2]([C:7]([Cl:24])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 70357o-Phenylbenzoic acid

Product 1

HCID 12563768[1,1'-Biphenyl]-2-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a dry nitrogen atmosphere 10 g (0.05 mole) of 2-biphenylcarboxylic acid was dissolved with stirring in 116 ml of dry toluene. Pyridine, 4.2 g (0.054 mole), was then added to the reaction mixture followed by 6.4 g (0.054 mole) of thionyl chloride. The reaction mixture was stirred at room temperature for two hours, then filtered to remove a white precipitate. The toluene was removed from the filtrate under reduced pressure to give [1,1'-biphenyl]-2-carbonyl chloride as a liquid residue, which was used without purification in Step B below.

Workup

  1. filtrationfiltered
  2. customto remove a white precipitate
  3. customThe toluene was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-0cb3e080d794456cb7fa51d3ea589eb7
Source dataset
uspto-grants-1984_09
Patent number
US04473709

Reaction notes

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