1-Chloro-4-(2,2-dibromoethenyl)benzene → 1-(Bromoethynyl)-4-chlorobenzene

HRID 1400611Notes

Reaction equation

HRID 1400611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9](Br)[Br:10])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.O>[Br:10][C:9]#[C:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 64229811-Chloro-4-(2,2-dibromoethenyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 6403901-(Bromoethynyl)-4-chlorobenzeneYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-chloro-4-(2,2-dibromovinyl)benzene (9.60 g, 32.7 mmol) in toluene was added potassium tertbutoxide (7.35 g, 65.6 mmol) at RT. The reaction mixture was heated at 80° C. for 3 h. The reaction was monitored by LCMS and TLC. The reaction mixture was diluted with water and extracted with EtOAc. The organic was dried over sodium sulfate and concentrated under reduced pressure to give the desired product (5.5 g).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af9eeb43a234499e9112352b1f32c4c5
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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