Bromine → Hydrogen Bromide

HRID 841052Notes

Reaction equation

HRID 841052 reaction equation
[CH2:1]([S:8][C:9](=[S:15])[NH:10][CH2:11][C:12]([Cl:14])=[CH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]Br>C(OCC)(=O)C>[BrH:16].[CH2:1]([S:8][C:9]1[S:15][C:12]([CH2:13][Br:16])([Cl:14])[CH2:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BrH:16]

Participants

5

Reactant 2

HCID 24408BromineHCID 54395229Benzyl (2-chloroprop-2-en-1-yl)carbamodithioate

Product 2

HCID 260Hydrogen BromideHCID 23450655HCID 23450655, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0.5 °C

Procedure

Under a slight stream of nitrogen, 19.9 g of (2-chloro-allyl)-dithiocarbamic acid benzyl ester are placed in 100 ml of ethyl acetate and cooled to 0-1° C. During the addition of bromine, the apparatus is flushed thoroughly with nitrogen. 14.0 g of bromine are added in the course of 40 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 20-250C. 50 ml of hexane are added, the mixture is filtered at 20-25° C., and the filtration residue is washed with 40 ml of hexane and dried in vacuo at room temperature. The title product is obtained in the form of the hydrobromide (compound 2.1).

Workup

  1. customthe apparatus is flushed thoroughly with nitrogen
  2. addition14.0 g of bromine are added in the course of 40 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 20-250C
  6. addition50 ml of hexane are added
  7. filtrationthe mixture is filtered at 20-25° C.
  8. washthe filtration residue is washed with 40 ml of hexane
  9. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-1efd337d0ebc4865b1881b0d13f9f6f3
Source dataset
uspto-grants-2002_04
Patent number
US06369233B1

Reaction notes

Loading…