N-bromobutanimide → HCID 18947676, compound

HRID 1591096Notes

Reaction equation

HRID 1591096 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([S:9][C:10]([F:13])([F:12])[F:11])[C:5]([Cl:14])=[C:4]([Cl:15])[C:3]=1[CH3:16].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:15][C:4]1[C:5]([Cl:14])=[C:6]([S:9][C:10]([F:12])([F:11])[F:13])[C:7]([Cl:8])=[C:2]([Cl:1])[C:3]=1[CH2:16][Br:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 18947698HCID 18947698, compound

Product 1

HCID 18947676HCID 18947676, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,3,5,6-tetrachloro-4-trifluoromethylthiotoluene (13.46 g, 0.041 mol) and N-bromosuccinimide (7.26 g, 0.041 mol) in carbon tetrachloride (34 ml) was stirred and heated at reflux for 21 hours. After cooling the mixture was filtered and the filtrate washed with aqueous sodium hydroxide solution (5%, 2×100 ml), water (100 ml), dried over anhydrous magnesium sulphate and evaporated to dryness. Recrystallization of the residue gave 2,3,5,6-tetrachloro-4-trifluoromethylthiobenzyl bromide (8.17 g) m.p. 117°-118.5° C. as a white crystalline solid. By proceeding in a similar manner but by replacing 2,3,5,6-tetrachloro-4-trifluoromethylthiotoluene with the following starting material there was prepared: 2-bromo-4-trifluoromethylbenzyl bromide as a mobile yellow oil from 2-bromo-4-trifluoromethyltoluene.

Workup

  1. temperatureheated
  2. temperatureat reflux for 21 hours
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered
  5. washthe filtrate washed with aqueous sodium hydroxide solution (5%, 2×100 ml), water (100 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated to dryness
  8. customRecrystallization of the residue

Sources & evidence

ORD record
ord-c4723a30aad84b9a83314137d37939a7
Source dataset
uspto-grants-1993_04
Patent number
US05206257

Reaction notes

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