Dimethylformamide → 4-(Pentafluorosulfanyl)benzoyl chloride

HRID 1458274Notes

Reaction equation

HRID 1458274 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[F:7][S:8]([F:21])([F:20])([F:19])([F:18])[C:9]1[CH:17]=[CH:16]C(C(O)=O)=[CH:11][CH:10]=1.CN(C)C=O>ClC(Cl)C.ClCCl.CN(C)C=O>[F:7][S:8]([F:18])([F:19])([F:20])([F:21])[C:9]1[CH:10]=[CH:11][C:1]([C:2]([Cl:4])=[O:3])=[CH:16][CH:17]=1

Participants

7

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27792104-(Pentafluoro-lambda6-sulfanyl)benzoic acid

Product 1

HCID 27792154-(Pentafluorosulfanyl)benzoyl chlorideYield 100.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
45 °C

Procedure

Oxalyl chloride (1.53 g) was added to a stirred solution of 4-pentafluorosulphanylbenzoic acid (0.99 g) in dichloroethane. A solution of N,N-dimethylformamide in dichloromethane (3 ml of a solution prepared by the addition of 2 drops of N,N-dimethylformamide to 10 ml of dichloromethane) was added. After 15 minutes the solution was heated for a further 15 minutes at 45° C., and evaporated to dryness to give 4-pentafluorosulphanylbenzoyl chloride as an orange oil (1.07 g). This was used directly in the subsequent reaction stage.

Workup

  1. additionwas added
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-101c7def415b4f0a9723497df61a8a3a
Source dataset
uspto-grants-1998_12
Patent number
US05849928

Reaction notes

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