Oxalyl chloride → HCID 19869782, compound

HRID 330328Notes

Reaction equation

HRID 330328 reaction equation
[F:1][C:2]1[C:3]2[O:14][CH2:13][O:12][C:9]([C:10]=1[F:11])=[CH:8][C:4]=2[C:5](O)=[O:6].C(Cl)(=O)C([Cl:18])=O>C(OCC)C.CN(C)C=O>[F:1][C:2]1[C:3]2[O:14][CH2:13][O:12][C:9]([C:10]=1[F:11])=[CH:8][C:4]=2[C:5]([Cl:18])=[O:6]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 19754838HCID 19754838, compound

Product 1

HCID 19869782HCID 19869782, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 15.0 grams (0.0742 mole) of 3,4-difluoromethylenedioxybenzoic acid in 200 mL of diethyl ether was stirred and cooled to 0° C. To this was added one drop of dimethylformamide followed by the dropwise addition of 11.3 grams (0.0890 mole) of oxalyl chloride. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature where it stirred for 60 hours. After this time the reaction mixture was concentrated under reduced pressure to yield 16.6 grams of 3,4-difluoromethylenedioxybenzoyl chloride.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureto warm to ambient temperature where it
  3. concentrationAfter this time the reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1abe99ae0a5441c9be0e40b366f274ac
Source dataset
uspto-grants-1990_01
Patent number
US04895871

Reaction notes

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