Bromine → 3'-Bromo-4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenyl

HRID 648868Notes

Reaction equation

HRID 648868 reaction equation
[CH3:1][CH:2]([CH2:27][CH3:28])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.[Br:29]Br.S([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:29][C:10]1[CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)(=[O:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[O:4][CH2:3][CH:2]([CH3:1])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 24408Bromine2×HCID 20143995HCID 20143995, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 201440033'-Bromo-4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenylYield 113.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenyl (41 g) prepared in the above step (ii) was dissolved in CCl4 (400 ml). To the resulting solution was dropwise added bromine (25 g) dissolved in CCl4 (100 ml), at room temperature over one hour, followed by stirring at room temperature for 5 hours, adding an aqueous solution of sodium hydrogen sulfite till the color of bromine disappeared, separating the organic layer, washing with 6N hydrochloric acid, washing with an aqueous solution of 2N NaOH, washing with water to make the solution neutral, drying and distilling off CCl4 to obtain oily 3'-bromo-4'-(2-methylbutyloxy)-4-p-toluenesulfonylbiphenyl (55.7 g).

Workup

  1. customseparating the organic layer
  2. washwashing with 6N hydrochloric acid
  3. washwashing with an aqueous solution of 2N NaOH
  4. washwashing with water
  5. customdrying
  6. distillationdistilling off CCl4

Sources & evidence

ORD record
ord-0bdd5c5951ed4243840eaf0e8229fe1c
Source dataset
uspto-grants-1988_04
Patent number
US04737313

Reaction notes

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