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

HRID 1731122Notes

Reaction equation

HRID 1731122 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-9fd886bdd2e541abb6d2ee8d2cce6825
Source dataset
uspto-grants-1976_11
Patent number
US03995042

Reaction notes

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