Bromine → Hydrogen Bromide

HRID 841053Notes

Reaction equation

HRID 841053 reaction equation
[C:1]1([S:7][C:8](=[S:14])[NH:9][CH2:10][C:11]([Cl:13])=[CH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:15]Br>BrCCl>[BrH:15].[Br:15][CH2:12][C:11]1([Cl:13])[S:14][C:8]([S:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:9][CH2:10]1.[BrH:15]

Participants

5

Reactant 2

HCID 24408BromineHCID 53931004HCID 53931004, compound

Product 2

HCID 260Hydrogen BromideHCID 23450653HCID 23450653, compound

Reagents, catalysts & solvents 1

HCID 6333BromochloromethaneSolvent

Conditions

Temperature
0.5 °C

Procedure

Under a slight stream of nitrogen, 18.4 g of (2-chloro-allyl)-dithiocarbamic acid phenyl ester are placed in 100 ml of bromochloromethane and cooled to 0-1° C. Before and during the addition of bromine, the apparatus is flushed thoroughly with nitrogen. 13.8 g of bromine are added in the course of 120 minutes in such a manner that the temperature can be maintained at 0-10° C. When the addition is complete, stirring is carried out for about 20 minutes. The reaction mixture is concentrated in vacuo at 20-25° C. 50 ml of hexane are added to the residue, and the product is filtered off with suction at 20-25° C., washed with 30 ml of hexane and dried in vacuo at room temperature. The title product is obtained in the form of the hydrobromide (compound 2.2).

Workup

  1. customthe apparatus is flushed thoroughly with nitrogen
  2. addition13.8 g of bromine are added in the course of 120 minutes in such a manner that the temperature
  3. temperaturecan be maintained at 0-10° C
  4. additionWhen the addition
  5. concentrationThe reaction mixture is concentrated in vacuo at 20-25° C
  6. addition50 ml of hexane are added to the residue
  7. filtrationthe product is filtered off with suction at 20-25° C.
  8. washwashed with 30 ml of hexane
  9. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-1f8719833e0f4b099368f0a22f9ac576
Source dataset
uspto-grants-2002_04
Patent number
US06369233B1

Reaction notes

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