Phosphorus pentachloride → (2-Bromophenyl)methanesulfonyl chloride

HRID 1523754Notes

Reaction equation

HRID 1523754 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([O-:12])(=O)=[O:10].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([Cl:15])(=[O:12])=[O:10]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23671425Sodium (2-bromophenyl)methanesulfonate

Product 1

HCID 2761452(2-Bromophenyl)methanesulfonyl chlorideYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of crude sodium (2-bromophenyl)methanesulfonate (34 g) in toluene (500 mL) was added PCl5 (34 g, 0.16 mol). The resulting mixture was stirred at 100° Celsius for 4 hours before concentrating to dryness and pouring the residue onto crushed ice (150 g), stirring for 5 min, and extracting with DCM (3×50 mL). The combined organic extracts were dried over MgSO4, filtered and concentrated to dryness to give (2-bromophenyl)methanesulfonyl chloride (16.8 g, 77%). 1H NMR (300 MHz, DMSO-d6) δ 7.62-7.45 (m, 2H), 7.29 (m, 1H), 7.18-7.01 (m, 1H), 3.97 (s, 2H).

Workup

  1. concentrationbefore concentrating to dryness
  2. additionpouring the residue
  3. customonto crushed ice (150 g)
  4. stirringstirring for 5 min
  5. extractionextracting with DCM (3×50 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e6a9eb4de1844c1d81a0dbd2e094bb30
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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