Phosphorus pentachloride → HCID 59623758, compound

HRID 1093942Notes

Reaction equation

HRID 1093942 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][S:13]([OH:16])(=O)=[O:14].[Na].P(Cl)(Cl)(Cl)(Cl)[Cl:19]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH2:12][S:13]([Cl:19])(=[O:16])=[O:14]

Participants

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 87086675HCID 87086675, compound

Product 1

HCID 59623758HCID 59623758, compoundYield 91.6%

Conditions

Temperature
85 °C

Procedure

A mixture of sodium (2-chloro-5-trifluoromethyl-phenyl)-methanesulfonic acid (Example 1.1) (9.4 g) and phosphorous pentachloride (13.5 g) was heated to 80-90° C. for 4 hours. The reaction mixture was concentrated. The residue was poured onto a mixture of ice and water and the mixture extracted twice with dichloromethane. The combined organic extracts were washed with water and brine, dried over magnesium sulfate and concentrated to give (2-chloro-5-trifluoromethyl-phenyl)-methanesulfonyl chloride as an off-white solid (8.480 g). 1H-NMR (400 MHz, CDCl3): 7.87 (m, 1H), 7.68 (m, 2H), 5.15 (s, 2H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe residue was poured onto a mixture of ice and water
  3. extractionthe mixture extracted twice with dichloromethane
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f80b9ea278394e7593b106a810eb1dc1
Source dataset
uspto-grants-2012_03
Patent number
US08133849B2

Reaction notes

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