Benzoyl Peroxide → 4-[(6-Acetoxyhexyl)sulfonyl]benzyl bromide

HRID 1633739

Reaction equation

HRID 1633739 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])(=[O:3])[CH3:2].[Br:21]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(F)(F)(F)F>[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][Br:21])=[CH:16][CH:15]=1)(=[O:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 186800254-[(6-Acetoxyhexyl)sulfonyl]toluene

Product 1

HCID 186800214-[(6-Acetoxyhexyl)sulfonyl]benzyl bromideYield 71%

Reagents, catalysts & solvents 1

HCID 6393Carbon tetrafluorideSolvent

Procedure

2.0 g of 4-[(6-acetoxyhexyl)sulfonyl]toluene, 1.3 g of N-bromo-succinimide (NBS), 0.015 g of benzoyl peroxide (BPO) , and 20 mL of carbon tetrafluoride were added to a 250 mL round bottomed flask and heated with reflux for 12 hours in nitrogen. The mixture was allowed to cool down and then filtered. The filtrate was washed by deionized water repeatedly. The organic fraction was dried over anhydrous magnesium sulfate and then concentrated by a rotary evaporator. The concentrate was further purified by re-crystallization to produce a white solid. The yield was 71% with the following structure.

Workup

  1. temperatureheated
  2. temperaturewith reflux for 12 hours in nitrogen
  3. temperatureto cool down
  4. filtrationfiltered
  5. washThe filtrate was washed by deionized water repeatedly
  6. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated by a rotary evaporator
  8. customThe concentrate was further purified by re-crystallization
  9. customto produce a white solid

Sources & evidence

ORD record
ord-d625cb0354ea4fdb9c0c5ba8db793974
Source dataset
uspto-grants-2003_01
Patent number
US06503998B2

Linked notes

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