N-bromobutanimide → HCID 14303120, compound

HRID 1761385Notes

Reaction equation

HRID 1761385 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][C:15]([CH3:24])([CH3:23])[C:16]([OH:22])([CH3:21])[CH2:17][CH2:18][CH:19]=[CH2:20])=[CH:12][C:11]=1[CH3:27]>C(Cl)(Cl)Cl>[Br:1][CH2:20][CH:19]1[CH2:18][CH2:17][C:16]([C:15]([O:14][C:13]2[CH:25]=[CH:26][C:10]([Cl:9])=[C:11]([CH3:27])[CH:12]=2)([CH3:23])[CH3:24])([CH3:21])[O:22]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 14303131HCID 14303131, compound

Product 1

HCID 14303120HCID 14303120, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

60 g (0.37 mol) of N-bromosuccinimide are added in portions to 88.8 g (0.3 mol) of 6-(4-chloro-3-methylphenoxy)-5-hydroxy-5,6,6-trimethyl-1-hexene in 600 ml of absolute chloroform, while stirring and cooling, so that the reaction temperature does not exceed 40° C. When the addition has ended, the mixture is stirred at room temperature for a further 14 hours and then washed twice with water and dried over sodium sulphate and the solvent is removed in vacuo. 94 g (82% of theory) of 2-bromomethyl-5-[2-(4-chloro-3-methylphenoxy)-prop-2-yl]-5-methyl-tetrahydrofuran are obtained and are further reacted without purification.

Workup

  1. temperaturecooling, so that the reaction temperature
  2. customdoes not exceed 40° C
  3. additionWhen the addition
  4. stirringthe mixture is stirred at room temperature for a further 14 hours
  5. washwashed twice with water
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-bc6a87ea02254d82bb52f99a5e2e74ab
Source dataset
uspto-grants-1989_05
Patent number
US04826836

Reaction notes

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