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

HRID 365046Notes

Reaction equation

HRID 365046 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.C(Cl)(=O)C([Cl:19])=O.CN(C=O)C>C1C=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:19])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 70357o-Phenylbenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirring solution of 1,1'-biphenylcarboxylic acid (1.0 g, 4.6 mmol) in 10 ml of dry benzene, under argon was added oxalyl chloride (0.40 ml, 2.0 eq.). To this solution was added DMF dropwise in 10 minute intervals, until no gas was evolved and the solution turned slightly cloudy (two drops). The mixture was stirred for 1 hour, then reduced on the rotovap without heating. The crude product, white solid, was carried directly on to the next step.

Workup

  1. temperaturewithout heating

Sources & evidence

ORD record
ord-077e64093e8844188c69ab64ccdd6654
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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