Sodium Hydroxide → (2,2-dibromoethenyl)benzene

HRID 905373Notes

Reaction equation

HRID 905373 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[C:5](Br)=[C:6](Br)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].[Br-:14].C([N+](CC)(CC)CCCCC)C>C(Cl)Cl>[Br:1][C:2]([Br:14])=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15919122N,N,N-Triethylpentan-1-aminium bromideHCID 197981311,2-Dibromo-3-(2-bromoethyl)benzene

Product 1

HCID 161726(2,2-dibromoethenyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 147.90 g. (0.431 mole) of 2-bromoethyl-dibromobenzene in 250 ml. of methylene chloride was stirred for 7 ks (2 hours) at 5 Hz (300 rpm) at 313 K. (40° C.) with 150 g (2.25 mole) of 60 percent sodium hydroxide solution and 3.12 g. (0.0124 mole) of triethylpentyl ammonium bromide. The product was washed with three 500-ml portions of water, dried over calcium sulfate (Drierite), and stripped of solvent in a rotary evaporator at a bath temperature of 323 K. (50° C.). The yield of product was 106.97 g. (77.2 percent of theory). GC analysis showed 27.1 percent of the desired ar-dibromostyrene, the remainder being largely unreacted starting material.

Workup

  1. custom(40° C.)
  2. washThe product was washed with three 500-ml portions of water
  3. dry with materialdried over calcium sulfate (Drierite)
  4. customstripped of solvent in a rotary evaporator at a bath temperature of 323 K
  5. custom(50° C.)

Sources & evidence

ORD record
ord-32c289c6daab45668f077a9f13b0e4cb
Source dataset
uspto-grants-1983_12
Patent number
US04423262

Reaction notes

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