Phosphorus pentachloride → 1-Bromo-2-[(chloromethyl)sulfanyl]benzene

HRID 461317Notes

Reaction equation

HRID 461317 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9]S(O)(=O)=O.[Na].P(Cl)(Cl)(Cl)(Cl)[Cl:16]>CCOCC>[Cl:16][CH2:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 24819Phosphorus pentachlorideHCID 5360545SodiumHCID 21393384HCID 21393384, compound

Product 1

HCID 218284941-Bromo-2-[(chloromethyl)sulfanyl]benzeneYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 60.4 g of [(o-bromophenyl)thio]methanesulfonic acid, sodium salt and 98.0 g of phosphorus pentachloride is blended until liquified, diluted with 600 ml of ether, and then poured on 1.2 kg of crushed ice. The ether layer is separated, washed, dried, and concentrated to give about 43.7 g of the named compound, bp about 86° (0.6 mm), mp about 28°-30°.

Workup

  1. customThe ether layer is separated
  2. washwashed
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbae775195484d5f9c6df2972d89f6f9
Source dataset
uspto-grants-1977_12
Patent number
US04062846

Reaction notes

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