2-Bromobenzenethiol → 1-Bromo-2-[(2-chloropentyl)sulfanyl]benzene

HRID 1658735Notes

Reaction equation

HRID 1658735 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].Br[CH2:11][CH:12]([Cl:16])[CH2:13][CH2:14][CH3:15]>C(O)C>[Cl:16][CH:12]([CH2:13][CH2:14][CH3:15])[CH2:11][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[Br:2]

Participants

5

Reactant 3

HCID 805982-BromobenzenethiolHCID 5360545SodiumHCID 13663922HCID 13663922, compound

Product 1

HCID 213933971-Bromo-2-[(2-chloropentyl)sulfanyl]benzeneYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 23.0 g of sodium metal is 500 ml of absolute ethanol is added, in about 0.5 hour, a solution of 173.0 g of o-bromothiophenol in 250 ml of absolute ethanol. The mixture is stirred and heated under reflux for about 0.5 hour, cooled to 0°, and treated, dropwise, with 185.5 g of 1-bromo-2-chloropentane. The addition requires about 1 hour. The mixture is stirred for about 2 hours at 0°, warmed slowly to reflux, and then heated under reflux for 2 hours. The mixture is filtered and the filtrate concentrated in vacuo at 40° to give about 255.7 g of o-bromophenyl 2-chloro-1-pentyl sulfide as a pale yellow oil.

Workup

  1. additionis added, in about 0.5 hour
  2. temperatureheated
  3. temperatureunder reflux for about 0.5 hour
  4. temperaturecooled to 0°
  5. additiontreated
  6. additionThe addition
  7. stirringThe mixture is stirred for about 2 hours at 0°
  8. temperaturewarmed slowly
  9. temperatureto reflux
  10. temperatureheated
  11. temperatureunder reflux for 2 hours
  12. filtrationThe mixture is filtered
  13. concentrationthe filtrate concentrated in vacuo at 40°

Sources & evidence

ORD record
ord-5e990209d35b480094f83b31cccef0aa
Source dataset
uspto-grants-1976_06
Patent number
US03966733

Reaction notes

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