Oxalyl chloride → 5-Fluoro-2-methylbenzoyl chloride

HRID 1978188Notes

Reaction equation

HRID 1978188 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1821145-Fluoro-2-methylbenzoic acid

Product 1

HCID 27373835-Fluoro-2-methylbenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-fluoro-2-methyl benzoic acid (2.31 g, 15.0 mmol) in dichloromethane (30 mL) containing a few drops of dimethylformamide was treated dropwise under nitrogen with oxalyl chloride (1.6 mL, 18.3 mmol). After gas evolution subsided, the reaction mixture was refluxed for an additional 10 minutes, and then evaporated to dryness. The crude acid chloride was used as such in the next step.

Workup

  1. temperaturethe reaction mixture was refluxed for an additional 10 minutes
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-de2fe5d6fd3741c487fe621778deafdc
Source dataset
uspto-grants-2001_05
Patent number
US06235900B1

Reaction notes

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