N-bromobutanimide → 5-Bromo-2,2-diphenyl-1,3-benzodioxol

HRID 1461081Notes

Reaction equation

HRID 1461081 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]1([C:15]2([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)(Cl)Cl>[Br:1][C:22]1[CH:21]=[CH:20][C:18]2[O:19][C:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:16][C:17]=2[CH:23]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 3439592,2-Diphenyl-1,3-benzodioxole

Product 1

HCID 223195155-Bromo-2,2-diphenyl-1,3-benzodioxol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

18.75 g of N-bromosuccinimide are added to a solution of 27.4 g of 2,2-diphenyl-1,3-benzodioxol in 80 ml of chloroform and the mixture was boiled at reflux for 20 hours. The reaction mixture was cooled and the separated succinimide was filtered off. The filtrate was washed with water, dried over sodium sulphate and the solvent was removed in a vacuum. By crystallization of the residue from ethanol, there was obtained 5-bromo-2,2-diphenyl-1,3-benzodioxol as white crystals of melting point 88°-89° C.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe separated succinimide was filtered off
  4. washThe filtrate was washed with water
  5. dry with materialdried over sodium sulphate
  6. customthe solvent was removed in a vacuum
  7. customBy crystallization of the residue from ethanol

Sources & evidence

ORD record
ord-1f40e0ed99974a8d8d8867f12beacd33
Source dataset
uspto-grants-1991_12
Patent number
US05073550

Reaction notes

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