Carbon Tetrachloride → HCID 43473032, compound

HRID 328631Notes

Reaction equation

HRID 328631 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:7]=1[CH3:15])[CH2:2][CH2:3][CH3:4].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[Br:39]N1C(=O)CCC1=O>O>[CH2:1]([O:5][C:6]1[C:7]([CH2:15][Br:39])=[CH:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 706687061-Butoxy-2-methyl-4-nitrobenzene

Product 1

HCID 43473032HCID 43473032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and gently refluxing mixture of 256 parts of butyl (5-nitro-o-tolyl)ether, 1 part of benzoyl peroxide and 4800 parts of anhydrous carbon tetrachloride is added, over a one-day period, a mixture of 213.6 parts of N-bromosuccinimide and 1 part of benzoyl peroxide. Upon completion, stirring at gentle reflux is continued overnight. The reaction mixture is cooled and water is added. The organic layer is separated, washed with water, dried, filtered and evaporated. The oily residue is crystallized on standing overnight in 2-propanol, yielding 189.7 parts of (α-bromo-5-nitro-o-tolyl) butyl ether; mp. 64° C.

Workup

  1. temperaturegently refluxing
  2. additionis added, over a one-day period
  3. stirringUpon completion, stirring
  4. temperatureat gentle reflux
  5. temperatureThe reaction mixture is cooled
  6. customThe organic layer is separated
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is crystallized
  12. waiton standing overnight in 2-propanol

Sources & evidence

ORD record
ord-aa16ddcb296046e8af79011b54127c7c
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

Loading…