Oxalyl chloride → 4-Fluoro-3-nitrobenzoyl chloride

HRID 2117010Notes

Reaction equation

HRID 2117010 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].C(Cl)(=O)C([Cl:17])=O>C(Cl)Cl.CN(C=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:17])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 27833474-Fluoro-3-nitrobenzoyl chlorideYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the 4-fluoro-3-nitrobenzoic acid (0.12 mol, 22.2 g) in 100 mL of anhydrous DCM was added 10 drops of anhydrous DMF. To this solution was added dropwise over 60 min, oxalyl chloride (0.144 mol, 12.6 mL). During the addition, the solid slowly dissolved to give rise to a yellow solution. The mixture was stirred for an additional 4 h and the solvent was stripped down to give a yellow oil. This oil was distilled under vacuum (110° C., 1.5 mm Hg) to give 4-fluoro-3-nitrobenzoyl chloride as a light yellow liquid (22.0 g, 90% yield).

Workup

  1. additionTo this solution was added dropwise over 60 min
  2. additionDuring the addition
  3. dissolutionthe solid slowly dissolved
  4. customto give rise to a yellow solution
  5. customto give a yellow oil
  6. distillationThis oil was distilled under vacuum (110° C., 1.5 mm Hg)

Sources & evidence

ORD record
ord-ccf8dbb2fbae4a4c81f2443c55f4998c
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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